Professional property managers have a systematic approach to tenant screening that helps them find reliable tenants who pay on time, take care of the property, and stay long-term. Here are the key steps they use, along with some "secrets" that set top property managers apart: 1. Standard Screening Process: Pre-Screening Questions:  Before showing the unit, property managers often ask key questions to weed out unqualified applicants (e.g., income, employment, reason for moving, move-in date). Credit Check:  They look for a credit score that indicates financial responsibility, often 650+ (but this varies by market). They also check for bankruptcies, late payments, and excessive debt. Income Verification:  Most require tenants to earn at least 3x the rent  in gross monthly income and verify this with pay stubs, W-2s, or tax returns. Employment Verification:  They contact employers to confirm job stability, role, and salary. Rental History:  Checking past landlords is crucial. They ask about payment history, lease violations, property condition upon move-out, and if the landlord would rent to the tenant again. Criminal Background Check (depending on the area):  They check for felonies, violent crimes, and drug-related offenses. Some jurisdictions have restrictions on what can be considered. 2. Secrets Used by Top Property Managers: They Call More Than Just the Current Landlord  – A tenant with a bad history might get a good reference from their current landlord who just wants them out. Smart managers call at least two  previous landlords. They Verify Landlord Authenticity  – Some applicants give fake landlord references (e.g., a friend pretending to be their landlord). Pro managers verify ownership records online or ask specific questions about the lease terms. They Check Bank Statements  – If applicants are self-employed or have irregular income, they check at least 3–12 months of bank statements  to confirm consistent deposits. They Look for “Tenant Red Flags” on Social Media  – Some property managers do a quick social media check to see if applicants are partying excessively, trashing prior apartments, or lying about pets. They Ask “Trick” Questions During Tenant Calls  – Instead of asking, “Do you pay rent on time?” they ask, “What date is rent due at your current place?” and “Have you ever been late on rent?” Honest tenants answer confidently; dishonest ones hesitate or change their story. They Offer Online Applications for Speed & Convenience  – The best tenants move fast. Online applications allow property managers to process screenings in hours instead of days. They Use Scoring Models & Automation  – Instead of gut feelings, they use tenant scoring models (e.g., RentPrep, AppFolio, Buildium) to ensure fair, consistent evaluations. Have questions, want to learn more, give us a call today!

Advertising a rental property in Chicago effectively requires a combination of high-traffic listing sites, local networking, and strategic marketing. Here are the our recommendations for the best ways to advertise and the top-performing rental listing sites  based on traffic and success rates Best Ways to Advertise Your Rental in Chicago List on High-Traffic Rental Sites   Focus on platforms with high visibility and renter engagement. Leverage Social Media & Facebook Marketplace   Chicago rental groups on Facebook can generate fast leads. Optimize Your Listing for SEO & Visibility   Use high-quality photos, detailed descriptions, and competitive pricing. Engage Local Real Estate Groups & Forums   Post in forums like BiggerPockets, Chicago real estate meetups, and Craigslist. Consider a Professional Leasing Agent   Leasing agents often have tenant pipelines and can help get your unit rented faster. Utilize Section 8 & Affordable Housing Platforms   Many renters actively search for Section 8-eligible units on specialized platforms. Place Yard Signs & Network Locally   Old-school methods still work—especially in high-traffic neighborhoods. Best Rental Listing Sites for Chicago These platforms have the highest traffic and success rates: Top General Rental Platforms Zillow Rental Manager  (High Traffic, Paid) Zillow, Trulia, and HotPads syndicate together. Best for:  High visibility, serious renters. Cost:  Free for the first listing, then ~$30 per listing per month. Apartments.com (CoStar Network)  (High Traffic, Free & Paid) Syndicates with ApartmentFinder, ApartmentGuide, etc. Best for:  High-end and mid-tier rentals. Cost:  Free basic listing; paid options available for premium placement. Facebook Marketplace  (High Traffic, Free) Best for:  Fast leads and direct tenant contact. Join local Chicago rental groups for added visibility. Craigslist Chicago  (High Traffic, Free & Paid) Best for:  Budget-friendly rentals, quick responses. Watch out for:  Scammers; be careful with tenant screening. PadMapper / Zumper  (Medium Traffic, Free) Best for:  Young professionals and digital-first renters. Realtor.com & Rent.com  (Medium Traffic, Paid) Good for professional listings and working with leasing agents. Niche & Specialized Platforms Chicago Housing Authority (CHA) Portal  – . AffordableHousing.com  – For government-subsidized housing. Domu.com  – Chicago-focused, attracts local renters. Airbnb / Furnished Finder  – If considering short-term or furnished rentals. Best Strategy for Fast Tenant Placement List on Zillow, Apartments.com , and Facebook Marketplace first. Cross-post on Craigslist, PadMapper, and Zumper. Section 8, list on AffordableHousing.com & CHA portal. Engage Chicago-based rental groups on Facebook. Consider using a leasing agent if the unit is vacant for too long.

1. Peak Leasing Season: March – September The busiest time for rentals in Chicago starts in March and peaks between May and August. The market stays strong through September, especially with students, young professionals, and families looking to move before the school year starts. Demand is highest during this time, leading to faster lease-ups, multiple applications, and higher rental rates. 2. Slower Season: October – February The rental market slows down significantly in the fall and winter, with the lowest activity in December and January. Renters during this period are typically relocating for work or need immediate housing, so pricing may need to be adjusted to attract tenants. Concessions (such as a free month of rent) are more common in winter to fill vacancies. How Long Does the Leasing Season Last? High-demand period: March – September (7 months) Slower period: October – February (5 months) If you list your rental between March and August, you're more likely to get top dollar, rent quickly, and secure strong tenants. Top Marketing Tools to Get the Best Price for Your Rental To attract high-quality tenants and secure the best possible rent, use a combination of digital marketing, professional presentation, and strategic pricing. 1. Professional Listing Photos & 3D Virtual Tours High-quality images increase engagement by 60% compared to low-quality photos. 3D virtual tours or video walkthroughs attract out-of-town renters and boost online visibility. 2. Listing on High-Traffic Rental Platforms Zillow, Apartments.com , HotPads, RentCafe, Craigslist, Facebook Marketplace, and PadMapper get the most rental traffic. Consider paying for premium listings on Zillow or Apartments.com during peak season to stand out. 3. Optimize the Listing Description Highlight unique features (in-unit laundry, stainless steel appliances, proximity to transit). Use SEO-friendly keywords like "pet-friendly," "modern kitchen," or "Wicker Park 2BR." Emphasize move-in readiness and incentives (e.g., "Move in by April 1 and get $500 off first month!"). 4. Competitive Pricing Strategy Research similar units in your neighborhood via Zillow Rent Zestimate, Rentometer, or local comps. If demand is high, consider listing slightly above market rate and adjusting based on inquiries. In slow seasons, offer flexible lease terms (e.g., 6-month lease or move-in specials). 5. Leverage Social Media & Word of Mouth Post your rental on local Facebook housing groups, Instagram, and Nextdoor. Offer current tenants a referral bonus for helping find a new renter. 6. Work with a Leasing Specialist or Property Manager A professional leasing agent can help price the unit accurately, market it widely, and handle showings & tenant screening. A full-service property manager ensures the unit is well-maintained and fills vacancies quickly. Final Takeaway: Timing & Strategy Matter List your rental between March and August to maximize demand and pricing. Use professional photos, high-traffic listings, and competitive pricing to attract the best tenants. If listing in the off-season (October – February), offer incentives like flexible leases or move-in specials.

Investing in multifamily properties in Chicago can be a game-changer for building wealth and generating passive income. But figuring out how to finance these properties—especially if you’re a first-time homebuyer or looking for owner-occupied options—can feel overwhelming. The good news? You don’t necessarily need 20% down, and there are flexible loan programs that can help you break into the market. At Teton Properties, we specialize in helping investors and owner-occupants navigate these financing options while providing full-service property management to make your investment as seamless as possible. Owner-Occupied vs. Non-Owner-Occupied Financing The financing options available to you will vary depending on whether you plan to live in the property or rent out all the units. Owner-Occupied Multifamily Loans : If you plan to live in one of the units, you can take advantage of lower down payment options, making it easier to acquire a property without a massive upfront investment. Non-Owner-Occupied Multifamily Loans : If you plan to rent out all units and not live in the building, traditional investment property loans typically require 15-25% down, but they come with fewer restrictions. First-Time Homebuyer Options: Lower Down Payments & FHA Loans First-time homebuyers in Chicago have additional advantages when purchasing a multifamily property (as long as it’s a four-unit building or smaller). FHA Loans : If the property qualifies, you may be able to purchase it with as little as 3.5% down. This is one of the best strategies for house hacking—living in one unit while renting out the others to cover your mortgage. Conventional Loans : Some conventional loan programs allow as little as 5% down for owner-occupied multifamily properties, though 15% is more common for duplexes and 25% for triplexes and fourplexes. Down Payment Assistance Programs : First-time buyers may also qualify for assistance programs that provide grants or low-interest loans to cover part of the down payment. The Power of Refinancing: Building Equity & Lowering Costs Once you’ve acquired your multifamily property, refinancing can be a key tool for optimizing your investment. If interest rates drop , you may be able to refinance to secure a lower mortgage payment. If you’ve added value to the property  (through renovations, improved management, or higher rents), you may qualify for a cash-out refinance to reinvest in additional properties or improve your current one. As long as you still live in the property , you can often refinance using owner-occupied loan programs, which tend to offer better rates and terms than traditional investment loans. You Don’t Need 20% Down – Finding the Right Deal Matters Many new investors assume they need a huge amount of cash to get started, but that’s not always the case. Whether you’re purchasing a turnkey property  that’s already cash-flowing or a value-add opportunity  that needs some work, the financing structure can look very different. An experienced mortgage broker can help you identify which loan products fit your situation best. Partnering with the Right Experts Having an experienced partner can make all the difference. A knowledgeable real estate broker will help you find properties that fit within the financing guidelines, and a reliable property management team will ensure your investment operates smoothly once you close the deal. At Teton Properties , we specialize in managing multifamily and mixed-use properties in Chicago, offering proactive management, personalized service, and competitive rates at just 5% per month. Whether you need help securing tenants, maintaining your building, or maximizing your investment, we’re here to help. Ready to Invest in Chicago Multifamily Properties? If you’re looking for expert guidance on purchasing and managing a multifamily property in Chicago, Teton Properties is your trusted partner . Contact us today to learn more about how we can help you achieve your real estate investment goals!

Why Real Estate Remains a Smart Investment During Market Uncertainty Market volatility can be nerve-wracking for investors, but real estate remains one of the most resilient asset classes—especially when managed strategically. Unlike stocks, which can fluctuate wildly due to economic uncertainty, well-selected multifamily and mixed-use properties can provide consistent cash flow regardless of market conditions. At Teton Properties , we specialize in full-service property management, brokerage, and leasing  to help investors navigate uncertain times and ensure their properties continue to perform. Whether you’re a seasoned investor or a DIY landlord, here’s why real estate can remain a solid investment even during economic downturns—and how working with the right team can help maximize your success. Cash Flow: The Key to Recession-Proof Real Estate One of the biggest advantages of real estate investing is that cash flow matters more than market value  in the short term. Even if property prices decline—like during the Great Financial Crisis—investors who owned cash-flowing properties  were still able to meet their mortgage obligations and generate income. How to Identify a Cash-Flowing Property: Strong Rental Demand  – Properties in desirable locations with stable tenant demand are more likely to maintain consistent cash flow. Reasonable Debt-to-Income Ratio  – Ensuring that rental income covers your mortgage and operating costs is key to weathering economic downturns. Long-Term Viability  – Look for properties in areas with strong job markets, population growth, and a track record of steady rental increases. At Teton Properties , our experienced brokerage team can help investors identify properties that cash flow  even in tough markets, setting them up for long-term success. How Property Management Helps Protect Your Investment Even a great investment property can quickly become unprofitable without proper management. High tenant turnover, prolonged vacancies, and deferred maintenance can erode cash flow, making it essential to have a proactive property management strategy  in place. Why Full-Service Property Management Matters: Minimizing Vacancy  – We leverage strategic marketing, thorough tenant screening, and quick turnaround times to keep your units occupied. Controlling Variable Costs  – Poorly managed properties often suffer from unreasonably high expenses. We ensure timely maintenance and efficient repairs to keep costs under control. Tenant Satisfaction & Retention  – Happy tenants are long-term tenants. We focus on responsive communication and proactive problem-solving  to foster positive landlord-tenant relationships. DIY landlords often underestimate the impact of poor management on their bottom line. Partnering with a professional Chicago property management company  like Teton Properties ensures that your investment remains profitable and low-stress  in any market. Why Experience Matters in Real Estate Investing The key to finding and managing a recession-resistant investment property is working with an experienced team that understands the nuances of multifamily and mixed-use properties . From identifying strong investments to managing day-to-day operations, the right advisors can make all the difference. How We Help Investors Like You: Expert Property Selection  – We help investors source and acquire properties with strong fundamentals. Strategic Management & Cost Control  – We ensure your asset performs optimally by keeping costs in check and maximizing rental income. Comprehensive Leasing Services  – Our leasing experts fill vacancies quickly with qualified tenants. Take Control of Your Investment Future Whether you're looking to purchase your first property or optimize an existing portfolio, working with a trusted property management and brokerage team  is essential. At Teton Properties , we provide the hands-on expertise needed to help investors succeed, even in uncertain markets. Are you ready to secure your financial future with recession-resistant real estate ? Contact us today to learn how Teton Properties  can help you maximize cash flow, protect your investment, and build long-term wealth.

The Human Side of Property Management: Why Empathy, Communication, and Relationship Management Matter In real estate investing, numbers matter—but people matter more. Whether you're a hands-on landlord or searching for a property management company in Chicago, your success isn't just measured by occupancy rates and cash flow. It's defined by the relationships you build, the trust you foster, and the homes you create for tenants. At Teton Properties we believe that effective property management goes beyond maintenance requests and rent collection. It’s about empathy, communication, and proactive relationship management —and here's why that matters. Empathy: The Key to Long-Term Success Being a landlord isn’t just about owning property—it’s about providing a home  for someone. Tenants aren’t just paying rent; they’re trusting you with their safety, comfort, and well-being . When property owners and managers approach their role with empathy, they see beyond the lease agreement and focus on creating a positive living experience. Why does this matter? Happy tenants stay longer, reducing turnover and vacancy costs. A tenant who feels heard and valued is more likely to care for your property . Understanding tenant concerns leads to proactive solutions , minimizing future issues. Communication: The Cornerstone of Trust A common frustration among tenants—whether renting from an independent landlord or a property management company—is lack of communication . When maintenance requests go unanswered or concerns are ignored, tenants feel unimportant and frustrated. At Teton Properties, we believe in open, transparent, and timely communication  to keep all parties informed and engaged. How we ensure effective communication: Clear Expectations : We set expectations upfront regarding lease terms, maintenance protocols, and tenant responsibilities. Proactive Updates : Instead of waiting for tenants to reach out, we provide regular check-ins and updates. Multiple Communication Channels : Whether it’s email, phone, or an online portal, tenants always have a way to reach us. For DIY landlords, prioritizing communication can mean the difference between a smooth, stress-free rental experience  and constant tenant disputes. Relationship Management: More Than Just Business Great property management isn’t just about fixing leaks—it’s about building relationships . The best landlords and property managers understand that fostering a positive landlord-tenant relationship leads to higher retention rates, better property care, and a stronger reputation . At Teton Properties, we: Prioritize tenant satisfaction  by responding quickly and addressing concerns with care. Create a sense of community  in multifamily and mixed-use properties, making tenants feel valued and respected. Support our property owners  by handling issues before they become costly problems, ensuring a win-win situation  for both landlords and tenants. Looking for a Property Manager Who Cares? If you’re a landlord who’s struggling with tenant retention, maintenance headaches, or communication gaps, you don’t need to do it alone. At Teton Properties, we provide full-service property management  with a focus on personalized attention, proactive solutions, and competitive rates . Our team is small enough to offer one-on-one care  but large enough to provide economies of scale , saving you money without sacrificing quality. Your investment is more than just a property—it’s a home for someone. Let us help you create a thriving, positive rental experience for both you and your tenants. Contact us today to learn more about how we can help you maximize your investment while ensuring your tenants feel safe, content, and valued. By prioritizing empathy, communication, and relationship management , landlords and property managers can elevate their rental experience from transactional to transformational. In an industry where homes are at the heart of what we do, putting people first isn’t just good business—it’s the right thing to do.

The Near North Side of Chicago is a vibrant and dynamic community, offering a blend of urban sophistication and historic charm. This comprehensive report provides insights into the current real estate market trends, property value appreciation, educational quality, and lifestyle factors that make the Near North Side an attractive option for potential buyers. Real Estate Market Trends and Price Appreciation As of January 2025, the Near North Side real estate market has demonstrated notable activity: Median Home Prices : The median listing price is $529,000 , reflecting a 3.8% decrease  compared to the previous year. Median Sold Prices : Homes have sold for a median price of $446,164 , marking a 4.2% increase  from the prior year. Price per Square Foot : The median price per square foot stands at $360 . Days on Market : Properties typically remain on the market for 93 days , slightly shorter than the 95 days observed last year. Sales Volume : In January 2025, 524 homes were sold, an increase from 441 homes  in the same month the previous year. These figures suggest a balanced market with steady demand and modest appreciation in property values. Educational Institutions The Near North Side is served by several reputable educational institutions: Public Schools : The area is home to various public schools, with test scores approximately 4% lower  than the national average. Selective Enrollment Schools : Proximity to esteemed institutions like Northside College Preparatory High School , which boasts a 10/10 GreatSchools rating , offers residents access to top-tier education. Lifestyle and Community The Near North Side offers a rich tapestry of lifestyle amenities: Cultural Attractions : Residents enjoy access to theaters, art galleries, and historic landmarks, contributing to a vibrant cultural scene. Dining and Shopping : The neighborhood boasts a diverse array of restaurants, cafes, and boutiques, catering to a wide range of tastes and preferences. Recreational Spaces : Proximity to Lake Michigan and numerous parks provides ample opportunities for outdoor activities and leisure. Conclusion The Near North Side of Chicago presents a compelling option for potential buyers seeking a blend of urban amenities, cultural richness, and educational opportunities. The real estate market reflects stability with potential for appreciation, making it an attractive investment. Prospective buyers are encouraged to explore current listings and engage with local real estate professionals to find properties that align with their preferences and investment goals.

Wrigleyville, nestled on Chicago's North Side, is renowned for its vibrant atmosphere, iconic Wrigley Field, and a rich tapestry of dining and entertainment options. This comprehensive overview delves into the current real estate market trends, property value appreciation, educational institutions, and lifestyle facets that make Wrigleyville a sought-after locale for potential buyers. Real Estate Market Trends and Price Appreciation As of January 2025, Wrigleyville's real estate landscape showcases robust growth: Median Home Prices : The median listing price stands at $609,000 , with homes typically selling for around $576,500 . Annual Appreciation : Over the past year, home values have appreciated by 5.6% , bringing the average home value to $532,749 . Market Dynamics : The area has experienced a 41.7% increase  in property listings between December 2024 and January 2025, indicating a growing inventory. Properties spend an average of 28 days on the market, reflecting a brisk sales environment. Educational Institutions Wrigleyville offers access to reputable educational facilities: Nettelhorst Elementary School : A magnet school known for its Gifted & Talented program, Nettelhorst has received an average performance rating compared to other public and charter schools in Illinois. Public High Schools : The neighborhood is served by several public high schools, with rankings based on state test scores, college readiness, graduation rates, and teacher quality. Lifestyle and Community Wrigleyville's dynamic lifestyle is a significant draw for residents: Entertainment and Dining : The neighborhood boasts a plethora of bars, restaurants, and music venues, catering to diverse tastes and preferences. Community Engagement : Residents enjoy a strong sense of community, with numerous local events and gatherings fostering neighborhood camaraderie. Recreational Spaces : Proximity to parks and Lake Michigan offers ample opportunities for outdoor activities and relaxation. Conclusion Wrigleyville seamlessly blends urban excitement with community charm, making it an attractive destination for potential homeowners. The upward trajectory in property values, coupled with quality educational institutions and a vibrant lifestyle, underscores the neighborhood's appeal. Prospective buyers are encouraged to explore current listings and engage with local real estate professionals to find a property that aligns with their preferences and investment goals.

A good property management company  typically charges fees based on the services provided. Here’s a breakdown of standard fees in Chicago and what to expect: 1. Monthly Management Fee This is the most important fee, covering day-to-day management , rent collection, tenant communication, and maintenance coordination. Single-Family & Small Multi-Units (2-4 units):   8%-12% of monthly rent Larger Multi-Family Buildings (5+ units):   5%-8% of monthly rent Flat Fee Option:  Some companies charge a fixed amount per unit, typically $100-$250 per month per unit Example: If your property rents for $2,000/month , expect to pay $160-$240/month  (at 8%-12%). For a 4-unit building renting at $1,500/unit , you might pay $480-$720/month  in management fees. 2. Tenant Placement (Leasing) Fee Covers advertising, tenant screening, lease signing , and initial move-in logistics. 50%-100% of one month’s rent Some charge a flat fee ( $500-$1,500 per unit ) Example:  If your rent is $2,000/month , a company might charge $1,000-$2,000 for placing a tenant. 3. Lease Renewal Fee Charged when a tenant renews their lease  (covers lease updates and negotiations). $100-$300 per lease Some charge 25%-50% of one month’s rent Example:  If rent is $1,800 , a 25% renewal fee would be $450 . 4. Maintenance Coordination Fee Some companies charge an extra fee (5%-10%)  on top of repair costs for coordinating maintenance and repairs . 5%-10% markup  on vendor invoices $25-$100 per maintenance request  (some charge per issue) Example:  A $500 plumbing repair  could cost $550 if there’s a 10% markup . 5. Eviction Fee (If Needed) Covers legal processing, court filing, and handling evictions. $500-$1,500 per eviction  (not including court fees) Full-service legal eviction  can cost $3,000+ 6. Inspection Fees Covers routine property inspections  (move-in/move-out, periodic inspections). $75-$250 per inspection Some include 1-2 free inspections per year 7. Miscellaneous Fees (Some Companies Charge Extra For) Onboarding Fee:  $250-$500 (one-time setup) Marketing Fee:  $100-$300 for professional photos/listings Vacancy Fee:  Some charge a flat fee during vacant months  (typically $50-$200/month) How to Get the Best Deal on Property Management Fees Negotiate lower rates  if you have multiple properties Look for all-inclusive pricing  (some companies bundle services for a flat rate) Ask about hidden fees  (markups on maintenance, admin fees, or vacancy charges) Avoid long-term contracts  without a trial period

Finding a good property management company  in Chicago requires due diligence to ensure they align with your investment goals. Here’s a step-by-step guide to finding a reliable, responsive, and effective property manager: 1. Define Your Needs Before searching, determine what services you require. Common property management tasks include: Marketing and tenant placement Rent collection and financial reporting Maintenance coordination Handling evictions and legal compliance Tenant communication and lease enforcement Since you’ve had issues with poor communication and lack of effort in marketing/tenant placement , prioritize responsiveness and proactive marketing strategies  in your search. 2. Ask for Recommendations Real Estate Investors & Landlords  – Network with other local landlords through BiggerPockets , Chicago real estate meetups , or local investor groups. Real Estate Agents  – Many agents work with or know reputable property managers. Facebook Groups & Forums  – Try Chicago Landlords Facebook groups , Reddit’s r/RealEstate  or local real estate forums. 3. Research Online Look up Chicago-based property management companies on: Google Reviews  – Search "best property management companies in Chicago"  and read reviews. Yelp  – Check for customer experiences and common complaints. Better Business Bureau (BBB)  – Look for complaints or bad business practices. National Association of Residential Property Managers (NARPM)  – Find certified property managers. Chicago Association of REALTORS®  – Some property managers are members, ensuring ethical standards. 4. Evaluate Their Services & Fees Contact at least 3-5 companies  and compare: Tenant Placement Fees  – Typically 50%-100% of the first month’s rent . Monthly Management Fee  – Ranges from 5%-12% of monthly rent  (lower for multi-unit buildings). Maintenance & Repair Handling  – Do they charge a markup? Do they have in-house maintenance or third-party vendors? Lease Renewal Fees  – Some charge $100-$300 or a percentage of rent . Eviction & Legal Fees  – Understand how they handle problem tenants. Red Flag   – Avoid companies that charge flat fees but provide poor service  (e.g., not actively marketing vacancies). 5. Check Their Marketing & Tenant Screening Process Since tenant placement was a previous issue for you, ask: Where do they list properties?  (Zillow, Apartments.com , Facebook Marketplace, local MLS?) How long do their properties stay vacant on average? What is their tenant screening process?  (Credit check, income verification, rental history?) Do they accept Section 8?  (If this is a priority for you) 6. Verify Responsiveness & Communication A good property manager should be easy to reach  and responsive. Test them by: Calling their office and noting how long it takes to get a response . Emailing as a “potential client” to see how quickly they reply . Asking how they communicate with landlords (portal, phone, email?). Red Flag   – If they take days to respond during the hiring process, expect the same when managing your property! 7. Review Their Contract Before signing, carefully review: Cancellation Terms  – Can you terminate the agreement easily? Fees & Extra Charges  – Ensure no hidden costs. Liability & Insurance Requirements  – Who covers damages? Tip  – Have a real estate attorney review the contract to avoid surprises. 8. Start with a Trial Period If possible, test their services  for a few months before committing long-term. Choose a company with month-to-month contracts  or a short initial term  (e.g., 6 months).

1. Legal & Compliance Understand Landlord-Tenant Laws – Familiarize yourself with federal, state, and local laws (e.g., security deposit limits, eviction procedures, tenant rights). Lease Agreement – Use a legally sound  lease with clear policies on rent, maintenance, pets, late fees, etc. Consider consulting an attorney. Fair Housing Laws – Avoid discrimination in tenant selection based on race, religion, family status, disability, etc. Required Disclosures – Be aware of lead-based paint disclosures (for homes built before 1978) and any local rental ordinances. Licensing & Permits – Some cities require rental property licenses or registration. Check local regulations. Proper Notices – Learn notice periods for rent increases, lease termination, and entry into the unit. 2. Tenant Screening & Lease Agreements Create a Tenant Screening Process – Require applications, credit checks, background checks, and rental history. Income Verification – Ensure tenants make at least 3x the rent  (varies by market). Ask for pay stubs or bank statements. Check References – Call previous landlords to ask about payment history, lease violations, and property care. Security Deposits – Follow legal guidelines for collection, storage, and return. Keep funds in a separate account. Have a Solid Lease Agreement – Clearly define: Rent amount and due date Late fees & penalties Maintenance responsibilities Pet policy Lease termination clauses Move-in Checklist – Document property condition before the tenant moves in with photos/videos. 3. Rent Collection & Finances Set Market Rent – Research comparable properties to set competitive rent. Use an Online Payment System – Reduce the hassle by using platforms like Zillow, Apartments.com , or Avail for automated payments. Enforce Late Fees – Be consistent with policies to avoid tenants taking advantage. Keep an Emergency Fund – Set aside 3-6 months of expenses  for repairs, vacancies, and unexpected costs. Track Income & Expenses – Use software like Stessa, Buildium, or QuickBooks for accounting. Understand Tax Deductions – Write off mortgage interest, property taxes, repairs, insurance, depreciation, and more. 4. Property Maintenance & Repairs Routine Inspections – Schedule periodic inspections to ensure the property is maintained. Respond Promptly to Maintenance Requests – Delays lead to bigger problems and unhappy tenants. Have a Reliable Handyman & Vendors – Build relationships with contractors for plumbing, electrical, and HVAC repairs. Landscaping & Curb Appeal – First impressions matter, even for rentals. Pest Control Plan – Preventative treatments save money over time. 5. Dealing with Tenants & Lease Violations Set Clear Expectations – Communicate house rules and enforce them consistently. Address Issues Early – Don’t let late payments, noise complaints, or lease violations slide. Maintain Professionalism – Treat tenants as clients, not friends. Handle Evictions Properly – If necessary, follow legal eviction procedures —never take matters into your own hands (e.g., locking out tenants). Cash for Keys Option – Instead of eviction, offer a small payout for tenants to leave voluntarily (saves time and legal fees). 6. Insurance & Risk Management Landlord Insurance – Standard homeowner’s insurance does not  cover rental properties. Get landlord-specific coverage. Require Renter’s Insurance – Protects your property in case of tenant negligence (e.g., fire, water damage). Liability Coverage – Ensure your policy includes liability protection in case of tenant injuries. Umbrella Policy – Extra protection for landlords with multiple properties. 7. Vacancy & Tenant Retention Market Your Rental Effectively – List on Zillow, Craigslist, Facebook Marketplace, and local rental sites. Professional Photos & Staging – Well-lit photos and clean spaces attract better tenants. Competitive Lease Renewals – Offer small rent increases  to retain good tenants instead of risking vacancy. Improve Tenant Experience – Quick responses, good maintenance, and respect lead to long-term tenants. 8. Long-Term Strategy & Scaling Plan for Future Investments – Use profits to reinvest in more properties. Build a Team – Consider a property manager as you scale. Network with Other Investors – Join local real estate meetups or online groups. Learn Creative Financing – House hacking, BRRRR, and partnerships can help expand your portfolio. Final Advice for First-Time Landlords Stay organized  with documents, leases, and tenant communications. Be firm but fair —don’t let tenants push boundaries. Treat your rental as a business , not a hobby. Continue learning —real estate laws and market trends change over time.

Self-managing a rental property in Chicago can be challenging, especially with the city’s specific laws, property maintenance requirements, and tenant relations issues. Below are the biggest challenges, with details on potential costs involved: 1. Tenant and Lease Laws Issue : Chicago has a complex set of tenant laws under the Chicago Residential Landlord and Tenant Ordinance (RLTO), which gives tenants substantial protections. These laws include rules on rent increases, security deposits, eviction, and maintenance responsibilities. Potential Costs : Legal Fees : If you're involved in a legal dispute, like a tenant not paying rent or violating the lease, you may incur legal fees. Attorneys in Chicago can charge anywhere from $200 to $500 per hour, depending on the complexity of the issue. Court Costs : Evictions or other legal actions may also involve court filing fees, which range from $100 to $400, plus additional fees for processing and serving notices. 2. Evictions Issue : Chicago’s eviction process is slower compared to other cities. Landlords can face delays and must follow strict procedures. For example, the "Just Cause" eviction ordinance requires a valid reason for eviction, and tenants can often delay the process. Potential Costs : Attorney Fees : Eviction cases can involve significant legal costs, often between $500 and $1,500 depending on whether the case is contested or uncontested. Court Filing Fees : As mentioned above, the cost of filing for eviction can range from $100 to $400. Lost Rent : The longer an eviction takes, the more rent you lose. For example, if the process takes 2-3 months, that could result in $2,000 to $3,000 in lost income (for a $1,000 per month rent). Tenant Damage : If the tenant leaves the property in poor condition or damages it, you may need to repair or replace items, which could cost $500 to $10,000 depending on the extent of the damage. 3. Property Maintenance and Repairs Issue : Chicago’s extreme weather can put a lot of stress on properties. Winters require snow removal, and summer humidity can cause mold or pest issues. Additionally, the city requires certain maintenance standards to ensure tenant safety. Potential Costs : Snow Removal : By law, landlords are responsible for snow removal. Depending on the size of the property, this can cost $200 to $1,000 per season for snow plowing and salting. Repairs : Common repairs like plumbing issues, HVAC maintenance, or roof leaks can range from $100 for a minor fix to several thousand dollars for major repairs (e.g., $2,000 for a new roof or $1,500 for an HVAC system replacement). Maintenance Staff : If you hire contractors or maintenance personnel, their hourly rates in Chicago can range from $50 to $150 per hour, depending on the service required (plumber, electrician, HVAC technician). 4. Security Concerns Issue : Some Chicago neighborhoods have higher crime rates, which may necessitate additional security measures to protect your property and tenants. Potential Costs : Security Systems : Installing a security system can cost between $200 to $1,500 for basic systems, or more if you include cameras, motion detectors, or 24/7 monitoring. Lighting : Additional outdoor lighting to deter crime may cost $50 to $200 per light installation. Security Personnel : Hiring security guards for regular patrols or events can cost between $20 to $50 per hour. 5. Rent Collection and Delinquencies Issue : Collecting rent on time can be a hassle. Late payments or missed payments may require follow-up, which takes time and can lead to lost income. Potential Costs : Collection Fees : If you hire a collection agency, their fees typically range from 25% to 50% of the collected amount. Late Fees : While you can charge late fees (usually $25-$50 in Chicago), tenants may dispute these charges, leading to potential legal or administrative costs. Lost Rent : If tenants are consistently late or miss payments, you may lose a significant amount of income. For example, a month of unpaid rent can be $1,000 or more. 6. Marketing and Tenant Placement Issue : Advertising for new tenants, conducting showings, and screening applicants all take time and effort. Potential Costs : Advertising : Listing fees on popular rental websites like Zillow or Apartments.com can range from $30 to $200 per listing. If you decide to use social media ads or print materials, these costs will increase. Tenant Screening : Screening tenants (criminal background, credit checks, rental history) often costs $25 to $50 per applicant, and you may have multiple applicants. Vacancy Costs : If you can't fill a vacancy quickly, you're losing rental income, which can range from $1,000 to $3,000+ per month, depending on the rent price. 7. Building Inspections and Code Compliance Issue : Chicago has strict building codes that landlords must comply with. Regular inspections and code enforcement can result in fines if things are not up to standard. Potential Costs : Inspection Fees : Inspections by the city can be required when renting out a unit, and failure to comply can result in fines ranging from $250 to $5,000, depending on the violation. Code Violations : If a property fails an inspection, you may have to make repairs or improvements to meet the code, which could range from $500 to $10,000 for structural fixes, electrical updates, or safety improvements. 8. Tenant Relations and Disputes Issue : Handling tenant complaints, disputes, or potential legal actions requires a professional approach. Poor communication or mishandling of tenant issues can lead to costly disputes. Potential Costs : Legal Fees : If a tenant decides to take legal action for issues like discrimination or safety violations, attorney fees can range from $200 to $500 per hour. Mediation or Arbitration : Mediation services can cost anywhere from $100 to $500 per session, depending on the mediator’s expertise. 9. Time Commitment Issue : Self-management is a full-time job. Managing emergencies, coordinating repairs, and dealing with tenant issues can quickly become time-consuming. Potential Costs : Opportunity Cost : The time you spend managing your property could be used for other income-generating activities or personal pursuits. If you’re spending 10 hours a week on property management, you might be losing out on $500 to $1,000+ in potential income (based on an hourly rate of $50 to $100). 10. Legal and Liability Risks Issue : Managing a property comes with inherent risks, especially when it comes to tenant safety or property damage. Potential Costs : Insurance : Landlord insurance typically costs between $500 and $2,000 per year, depending on the coverage level and property type. Legal Fees and Settlements : If you're sued (e.g., a tenant sues for injury or illegal eviction), legal fees can easily range from $1,000 to $10,000 or more, depending on the case complexity. Conclusion Self-managing a property in Chicago can be financially rewarding if done correctly but comes with significant costs and risks. It's important to weigh the time commitment and potential financial burden against the benefits of having more control over your property. If you prefer to avoid these issues, hiring a property management company may be a good option, although it typically costs around 8% to 12% of the monthly rent, plus additional fees for services like leasing or maintenance coordination.