Advise for a New Investor

Advise for a New Investor

Chicago, IL · Member since 2021 · 39 posts · 9 votes

Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?

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Bo SmithPro Member
Hinton, WV · Member since 2026 · 1k+ posts · 373 votes
7mo

Section 8 in south suburbs can be tricky - I'd honestly connect with local property managers first before even picking financing. They'll tell you which streets actually work and what rents look like in reality. Most people jump straight to the money part but those PM relationships are gold. You talking to any managers down there yet?

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  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    7mo
    Welcome! It depends on how much equity sprea you create and how much cash you can leave in the deal. Usually when you’re refinancing out of hard money, you’ll get 75% LTV. How much cash could you afford to leave in the deal if you needed to? How much value are you typically trying to add after purchase?
    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

      @Aaron Zimmerman, those are great questions. I don't know how to answer the first question correctly, and for the second question, I'd need to add enough value to ARV to make the deal make sense for a hard money lender and me.

  • Stacy RaskinBusiness Member
    Lender · Member since 2022 · 1k+ posts · 505 votes
    7mo

    Investors generally will either use their own money or will use a hard money loan to acquire a property that needs repairs. There are some hard money lenders that will lend up to 90% of the purchase price and 100% of the rehab that's done on draws depending on the borrower credit and the location of the property. Once the property is rehabbed, an investor if they have taken a hard money loan will take out a conventional loan or a DSCR loan to pay off the hard money loan (HML) to convert the HML loan to a long term loan. DSCR loans have less paperwork and there's a shorter waiting period between transactions- also called a shorter seasoning period. Usually investors are looking to pull out their cash on the after repair value (ARV) so they are looking for a shorter seasoning period to get their cash out for the next deal. Working with a mortgage broker who specializes in HML loans and DSCR loans can be helpful as there are many DSCR and HML lenders who don't advertise directly to the public. Specialized investment programs can help an investor with more favorable terms and rates.

    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

      @Stacy Raskin, could you please connect me with some mortgage brokers you recommend for these types of loans? Also, what are the requirements to qualify for a DSCR loan?

    • Stacy RaskinBusiness Member
      Lender · Member since 2022 · 1k+ posts · 505 votes
      7mo
      Quote from @Jamarius Everett:

      @Stacy Raskin, could you please connect me with some mortgage brokers you recommend for these types of loans? Also, what are the requirements to qualify for a DSCR loan?


      I'm a mortgage broker. The requirements are largely based around borrower credit score and LTV but requirements can sometimes vary by the state as the lenders are regulated by each state.

  • Lender · Member since 2021 · 495 posts · 130 votes
    7mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?

    The shorter seasoning period makes a DSCR loan a popular option for the refinance once the property is rehabbed.
    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

      @Andrew Zamboroski, thanks for the advice.

  • Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
    7mo

    @Jamarius Everett

    Hard money for the purchase and shop around for the refinance.

    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

       @Paul De Luca, thanks and the advice.

  • Ben FernandezBusiness Member
    Realtor · Lancaster, PA · Member since 2025 · 169 posts · 97 votes
    7mo

    Use both when BRRRR'ing. Hard money to enter and traditional financing or a DSCR loan on the refi/long-term hold.

    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

      @Ben Fernandez, thanks for the insight.

  • Nick BelskyBusiness Member
    Residential and Commercial Broker · Member since 2021 · 1k+ posts · 704 votes
    7mo

    @Jamarius Everett

    We work with a variety of HML for BRRRR deals. Would be happy to connect and talk financing shop anytime.

    Cheers!

    Belsky Mortgage, LLC527 Reviews
  • Bo SmithPro Member
    Hinton, WV · Member since 2026 · 1k+ posts · 373 votes
    7mo

    Section 8 in south suburbs can be tricky - I'd honestly connect with local property managers first before even picking financing. They'll tell you which streets actually work and what rents look like in reality. Most people jump straight to the money part but those PM relationships are gold. You talking to any managers down there yet?

  • Attorney · Chicagoland · Member since 2021 · 12 posts · 7 votes
    7mo

    Know that Calumet City has rules/ordinances that must be met BEFORE a Tenant can occupy a property.
    rental-process.pdf
    You could/should connect with the Building Department and/or Seller to learn before buying as to whether or not the property will pass a City Inspection.

    Ask Seller, if it is currently rented, about whether or not the current Tenant is on Section 8 (learn about requirements for transfer to you as new Owner) and confirm that Seller has correctly renewed his current annual rental business license.  

  • Specialist · Member since 2026 · 53 posts · 25 votes
    7mo

    Since you’re early in scaling, I’d try to separate financing mechanics from deal quality. In places like Calumet City, I think the bigger driver is whether the deal still works when you underwrite it conservatively — realistic Section 8 rents, higher maintenance, vacancy between tenants, and some friction in refi timing.

    Hard money vs bank financing both have a place, but I’d personally start by underwriting deals assuming less-than-perfect execution and seeing if there’s still margin. If a BRRRR only works with tight timelines, top-end rents, and a smooth refi, that’s usually where risk shows up — regardless of the lender.

    For Section 8 especially, I think focusing on durability (property condition, management, reserves) matters more early on than trying to optimize leverage. The financing choice tends to become clearer once the numbers hold up under conservative assumptions.

    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

      @Pavel Voroniuk, okay, and thank you for the insight.

  • Member since 2025 · 244 posts · 99 votes
    7mo

    @Jamarius Everett Calumet City is a cash-flow heavy hitter! Scale using Hard Money for speed and rehab, then refi into DSCR bank loans. Focus on 3+ bedrooms to maximize Section 8 vouchers.

    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      7mo

      @Kate Sanchez, thanks for the advice.

  • Lender · Chicago, IL · Member since 2025 · 204 posts · 101 votes
    7mo

    You are targeting a proven rental market and a strategy many investors use to build cash-flowing portfolios. Section 8 rentals and BRRRR investing in areas like Calumet City are commonly used for portfolio growth, long-term cash flow, and scalable real estate investing when executed correctly.

    I will share this from both my experience as a real estate investor and as a mortgage loan officer for over 25 years.

    Section 8 can be a strong strategy in areas like Calumet City because demand is steady and voucher payments can provide consistent rent. The key is buying right and managing well. Not every property or tenant scenario performs the same, so your screening, inspections, and property management systems matter just as much as your financing.

    On the BRRRR side, your financing choice should match your exit strategy and your risk tolerance.

    Hard money can make sense when:

    • You need to close fast

    • The property needs significant rehab

    • The deal is distressed and will not qualify for traditional financing upfront

    • You have a clear and realistic refinance plan

    Hard money is a short term tool. Higher rates and fees mean the numbers have to be solid, and your timeline needs to be realistic. I have seen newer investors get in trouble when rehabs or appraisals take longer than expected.

    Bank or conventional financing can be great when:

    • The property is already in decent condition

    • You qualify with income, credit, and reserves

    • You are focused on long term holds

    • You want lower cost of capital

    For many BRRRR investors, the winning formula is a combination. Use hard money or private money to acquire and rehab, then refinance into a conventional or DSCR loan once the property is stabilized and rented.

    A few practical tips for your area and strategy:

    • Know Calumet City rents and realistic ARVs block by block

    • Build relationships with local inspectors and contractors

    • Understand Section 8 inspection standards ahead of time

    • Keep solid reserves, especially with older housing stock

    • Do not over leverage just because numbers look good on paper

    The investors who scale successfully in the south suburbs treat this like a business. They track numbers closely and stay conservative with projections.

    A few questions to ask yourself as you grow:

    Do your deals still cash flow if maintenance and vacancies run higher than expected?

    Are you building reserves as you scale or using every dollar for the next deal?

    Is your refinance plan realistic based on today’s lending environment?

    If you ever want a second set of eyes on deal structure or financing options, I am always open to sharing insight and helping investors think through scenarios. Sometimes a quick review upfront can save a lot on the backend.

  • Mackaylee BeachPro Member
    Real Estate Agent · Kansas City, MO · Member since 2020 · 1k+ posts · 492 votes
    7mo

    When considering the best financing options for your BRRRR strategy, you might want to weigh the pros and cons of both hard money lenders and traditional bank financing.

    Hard money lenders can offer quick access to funds, which is particularly useful when you need to act fast on a promising property. They often require less stringent credit checks and provide more flexible terms. However, the interest rates are typically higher, and the loan terms are shorter, which can add pressure to refinance quickly.

    On the other hand, bank financing usually comes with lower interest rates and longer terms, potentially offering more stability. Banks will likely require a more thorough vetting process, including credit checks and detailed financial documentation, which can take time.

    • Chicago, IL · Member since 2021 · 39 posts · 9 votes
      6mo

      @Mackaylee Beach, thanks for the advice. 

  • Real Estate Agent · Chicago · Member since 2021 · 168 posts · 62 votes
    7mo

    Hey Jemarius, welcome to the journey! A bit about me: I own 21 properties, manage a team doing $88M/year in sales, and have helped tons of buyers around your age on BiggerPockets get started and scale their portfolios.

    For Calumet City and Section 8 rentals:

    • Section 8 can provide steady cash flow, but make sure you run the numbers conservatively (account for vacancies, repairs, and inspection timelines).

    • Bank financing is generally cheaper long-term and lets you scale more sustainably. Hard money can speed up BRRRR deals but comes with higher costs, so I usually reserve it for deals that need fast rehab or are hard to get financed otherwise.

    • Focus on deal quality and cash flow first, then think about leveraging different financing strategies as you grow.

    • Always have a system for evaluating properties, tracking expenses, and managing tenants, it’s what allows you to scale efficiently.

    If you want, I can share some tips specific to BRRRR in the Chicago suburbs that have worked for my team and clients. You're in a great spot to start building momentum.

  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    7mo

    Hi there @Jamarius Everett - First question, what's your "WHY" behind that stratagy of doing LTR section 8 rentals in calumut city?

    Great Chicago south suburb, but just curious about your reasoning because your strategy and why is the first thing you need to nail.  Also, you might have to answer that question of WHY several times to get to the root why!

    If you can do hard money for the rehab and then refi out with conventional bank financing, that will probably be the best result.  I'd be happy to make some intros to some of my connections if that would be helpful! 

  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 929 votes
    7mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?

    @Jamarius Everett

    Great to see you thinking strategically about scaling. Calumet City and the south suburbs can work for Section 8, but cash flow and BRRRR execution can be tight with high entry prices. If you're open to out-of-state options, Midwest markets often let you buy undervalued duplexes or small multis that cash flow immediately, making BRRRR deals smoother and less stressful. Focus on stable neighborhoods, solid numbers from day one, and building a reliable local team to scale efficiently.

  • James JonesPro Member
    Investor · Collierville, TN 38017 · Member since 2017 · 635 posts · 461 votes
    7mo

    If you are targeting Calumet City with a Section 8 focus, you need to think in terms of systems, not just deals.

    A few strategic points:

    Know your payment standards before you buy

    Call the local housing authority and pull current payment standards for 2 bed and 3 bed units.

    In voucher heavy markets, your ceiling is not just market rent. It is rent reasonableness plus payment standard.

    Buy at a price that still works even if you are slightly under the max.

    Micro location matters even in voucher markets

    Do not assume “it’s Section 8, location doesn’t matter.”

    In South Suburbs:

    • School zones

    • Crime pockets

    • Proximity to retail and transportation

    • Block by block condition

    These impact quality of applicant pool and long term stability.

    Focus on 3 bed houses if the numbers work

    In many Chicago suburb voucher markets, 3 beds have:

    • Strong demand

    • Higher payment standards

    • Better long term tenant stability

    Run the numbers carefully on taxes though. Property taxes in Cook County can destroy your margin if you ignore reassessment risk.

    BRRRR strategy in this area

    The risk in Calumet City is ARV overestimation.

    Banks are conservative on appraisals in certain South Suburb pockets. If your ARV comes in light, your refinance stalls and your capital gets trapped.

    Underwrite conservatively:

    • Expect lower appraisals than retail comps

    • Budget realistic rehab

    • Leave margin for tax increases

    Hard money vs bank for BRRRR

    Hard money makes sense when:

    • You are buying distressed

    • You need speed

    • Seller won’t wait

    • Rehab is heavy

    But you must have a clear refinance exit.

    Local banks or credit unions can be strong refinance partners if:

    • You build a relationship

    • You keep solid reserves

    • Your debt to income is clean

    Long term, relationship banking is cheaper capital. Hard money is a tool, not a strategy.

    Protect your scaling pace

    In lower price point markets, it is easy to buy several properties quickly.

    But scaling without:

    • Solid reserves

    • Strong property management systems

    • Clear screening standards

    Will backfire fast.

    Especially in Section 8 heavy portfolios, inspection compliance and turnover control determine your success.

    If I were starting fresh there, I would:

    • Lock in one clean BRRRR deal

    • Refinance successfully

    • Prove appraisal and rent assumptions

    • Build banking relationship

    • Then scale deliberately

    In that market, discipline beats speed.

    Cash flow looks great on paper in the South Suburbs. The investors who win long term are the ones who manage taxes, inspections, and tenant screening tightly.

  • J CastroBusiness Member
    Lender · Florida · Member since 2025 · 684 posts · 246 votes
    7mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?

    Hey @Jamarius Everett, welcome to investing, and great choice targeting the Chicago south suburbs! Calumet City has strong Section 8 demand, which can provide consistent cash flow, but scaling there effectively requires a solid strategy.

    Here are some tips:

    1. Financing: Hard Money vs Bank

    • Hard Money Lenders: Great for fast acquisitions and heavy rehabs. They're flexible, approve quickly, and work well if you're doing multiple BRRRR deals and need to move fast. The tradeoff is higher interest and fees, so plan your rehab budget and exit carefully.

    • Bank Financing: Conventional or portfolio loans typically have lower rates and longer terms. Once you've rehabbed and stabilized the property, converting from hard money to bank financing for the "R" in BRRRR (Refinance) can maximize cash flow and equity.

    2. BRRRR Strategy in Section 8 Markets

    • Make sure your rehab budget aligns with local Section 8 standards — units need to meet HUD inspection requirements.

    • Target properties where after-repair rents are competitive but not overpriced; Section 8 vouchers have set limits.

    • Document your process and tenant management approach — investors and lenders like to see systems in place.

    3. Scaling Tips

    • Focus on building a team: property manager familiar with Section 8, contractor, lender.

    • Start with 1–2 properties, get them stabilized, then leverage equity and proven cash flow for the next acquisitions.

    • Keep an eye on neighborhoods with strong rental demand and lower vacancy rates — Calumet City has pockets of high demand.

    In short: use hard money to acquire and rehab quickly, then refinance through a bank or portfolio lender to lower your carrying costs and repeat the BRRRR cycle.

    Best of luck with your portfolio — keep us posted on your progress! Calumet City can be a strong market for scaling smartly with Section 8 rentals.

    JCREIG Capital Funding
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    7mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?


     Why does every new investor think Section 8 is the way to go?

    How much research about S8 negatives have you done here on BP?

  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    7mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?

     Here's a recent post by @Eric Fernwood:

    Section 8 sounds like guaranteed income—no fuss, no muss. We’ve had a few clients try Section 8 and the results were disastrous. Note that I am writing about Section 8 in Las Vegas, where you are considering investing may be completely different.

    The situation in Las Vegas

    • "Guaranteed" income: Not quite. The government typically pays 80% while the tenant pays 20%. Clients who've tried Section 8 report they almost never receive the tenant's 20% portion. When I asked a property manager I respect whether we should evict these tenants, she said there was no point—Section 8 tenants rarely pay their 20%.
    • Maintenance costs: Clients with Section 8 properties regularly complain about high maintenance expenses. Section 8 performs inspections, and if anything doesn't meet their requirements, your payments stop. Some tenants use this as leverage to get what they want. For example, one tenant demanded all new stainless steel kitchen appliances. The owner refused. The tenant then systematically broke windows and reported the damage to Section 8. The owner had to replace the windows to resume payments. The tenant broke them again. This cycle of property damage and Section 8 complaints continued until the owner finally installed the stainless steel appliances. Significant property damage is common with Section 8 tenants.
    • One client rented a single-family home through Section 8 for $50 more per month than market rate. He bragged about the extra income. After a year of high maintenance costs—largely from vandalism—he chose not to renew the lease. Once the tenant moved out, restoring the property to livable condition cost him over $15,000.
    • A client who had purchased multiple properties from us and made good money attended a real estate convention where he learned that the secret to great wealth was multifamily properties with section 8 tenants. To make a long story short, he's in bankruptcy now due to the losses from these properties.

    You need to do research where you plan to invest and not listen to the opinions of others. I recommend talking to multiple property managers who are managing section 8 properties and getting their read on the situation. Perhaps it is totally different than what happens in Las Vegas.

  • Mike FisherBusiness Member
    New Lenox, IL · Member since 2024 · 101 posts · 56 votes
    7mo

    Jamarius, welcome. Calumet City can work for Section 8, but it is a market where execution matters more than theory.

    A few things to focus on before you decide hard money versus bank financing.

    1. Know your real rent ceiling, Voucher rent is limited by payment standards plus rent reasonableness, and the unit has to pass inspection. Underwrite to what is consistently getting approved, not the highest number you see online.

    2. Micro location is everything, It is block by block. Tenant quality, turnover, and inspection friction can change fast within a small radius. Do not treat the whole town as one rent and risk profile.

    3. Underwrite taxes and refi appraisals conservatively, Cook County taxes and conservative appraisals in certain pockets are what break BRRRR here. If the refinance comes in light, your capital gets trapped. Assume the appraisal is lower than the best retail comps and leave margin.

    4. Build the team before you scale, Section 8 success comes down to systems. Screening, inspection prep, maintenance response time, and documentation. If those are not tight, cash flow can look great on paper and still turn into a headache.

    Hard money versus bank for BRRRR, Hard money is usually the tool for acquisition and rehab when you need speed or the property will not qualify for bank financing as is. The long term strategy is typically to refinance into cheaper bank or credit union debt once the unit is stabilized and performing. Hard money is expensive, so the key is having a realistic refi plan and conservative after repair value assumptions.

    If you are new, I would do one deal, stabilize it, and see how the inspection timeline, rent approval, taxes, and appraisal actually play out. Once you have that proof, scaling gets much easier and much safer.

    M Property Group LLC | MF Cashflow Property Management4.9102 Reviews
  • Member since 2023 · 28 posts · 11 votes
    7mo

    How distressed are these investment properties that you are buying? How much work are you doing yourself/hiring out? How much do you have for renovations? Answering those questions will help get you a lot closer to your answer. 

  • Investor · Nashville · Member since 2026 · 37 posts · 11 votes
    7mo

    Welcome! Calumet City can work well for Section 8 if you’re buying at the right basis and really dialing in tenant screening and property management. On BRRRRs, hard money is usually helpful for speed and renovations, then refinance into bank financing once stabilized — but the numbers have to support the refi.

  • Financial Advisor · FL · Member since 2024 · 442 posts · 100 votes
    6mo

    Most people are overthinking the financing part.

    In your case, it's pretty simple. Use hard money when the deal needs speed or heavy rehab, then refi into DSCR or bank debt to hold. That's the clean BRRRR path and it's what a lot of investors in your market are doing .

    What actually matters more is the deal. In Calumet City, if your numbers don’t hold with conservative Section 8 rents, longer inspection timelines, and higher maintenance, the financing won’t save you.

    Focus on buying right and knowing your true ARV and rents. The financing choice becomes obvious after that.

    If you want, send me a deal you’re looking at and I’ll help you break it down.

    Stevan

  • Alfath AhmedBusiness Member
    Real Estate Agent · Columbus, OH · Member since 2022 · 1k+ posts · 1k+ votes
    6mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?


    I use hard money for all my projects. I have some good HML lenders that I can connect you with. If you have about $40k to $50k in starting capital. You are good to run projects and have enough for down payment + security.

    I've got 28 rental units in my market and grew my portfolio by doing the brrrr method. Reach out if you have any questions.

  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 929 votes
    6mo
    Quote from @Jamarius Everett:

    Hello everyone, I'm a new investor looking to expand my real estate portfolio in the Chicago south suburbs, preferably Calumet City, with a focus on section 8 rentals. Do you have any advice that would be useful for growing and scaling my portfolio in Calumet City? Specifically, should I focus on using hard money lenders or bank financing when doing BRRRR deals?


    For starting out, focus on building a few strong, cash-flowing rentals first and get really comfortable with the numbers and rehab process. Hard money can be useful for speed, but bank financing is usually cheaper long-term if you can qualify. If you’re open to out-of-state investing, Midwest markets have undervalued Section 8-friendly properties with predictable cash flow and strong long-term upside, plus it’s easier to scale with a solid local team handling rehabs and property management.
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