1st time home buyer

Chicago, Illinois
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1st time home buyer

Leti Salas
Member since 2026 · 6 posts · 4 votes

Hello,

I'm in the market to buy my first home and start building my real estate portfolio.  Im currently working in Mount Pleasant,  WI.  Im paying 1800 a month in rent, as Im here during the week. I live in Chicago and my rent through a family member is 800. I go home weekends. Im not sure if I should buy a multi unit in Chicago and house hack in the 500-700k range or buy in WI in the 400k range and get rid of the rent here. Ill be working here about 2-3 years. Any advice is appreciated. 

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  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    3mo

    What has you in Chicago? Family? 

    could you buy a house hack in the northern suburbs like Waukegan or wauconda?

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  • G. Brian DavisPro Member
    Investor · Hatboro, PA · Member since 2016 · 2k+ posts · 853 votes
    3mo

    If your plan is only 2–3 years in Wisconsin, I’d lean toward Chicago for a house hack.A multi-unit there gives you experience managing tenants, building equity, and cash flow and you can always rent it out later if you move. Buying in Wisconsin might save you rent short-term, but with a shorter timeline, the upside of a proper house hack in your home market usually outweighs it.

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  • Mohammed Rahman
    Real Estate Broker · New York, NY · Member since 2020 · 2k+ posts · 1k+ votes
    3mo

    Hello Leti,

    If you're only planning to be in Wisconsin for another 2-3 years, I'd spend some time thinking about where you want to own property long term, not just where you're working today.

    Personally, I'd lean toward the market where you ultimately want to build your portfolio and have a long-term presence. House hacking a multifamily can be a great way to get started, but only if the property still makes sense as a rental after you move out.

    I'd run the numbers both ways and ask yourself: "Which property would I rather own five years from now?" That answer may be more important than where you're sleeping during the work week.

    I'm a real estate broker based in NYC and Long Island. Happy to share ideas and answer questions. Feel free to reach out anytime, my DMs are always open!

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  • Leti Salas
    OP
    Member since 2026 · 6 posts · 4 votes
    3mo

    Family and Friends. Im open, just looking where my first home and investment property will be. Hoping to start a small portfolio for retirement.  Im divorced and rebuilding my life. Im in a decent spot, not sure what makes most sense

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  • Leti Salas
    OP
    Member since 2026 · 6 posts · 4 votes
    3mo

    Hi,

    I appreciate the information.  Ive ran some numbers with my mortgage lender and I'm looking to basically swap my Chicago rent into a mortgage,  which Im only paying 850. I live in a small apartment above my Sister in their home. Its been wonderful. However, Ive been wanting to get into the market for obvious reasons.  Bulid equity, set myself for retirement,  etc. This is my first home I will be purchasing. Im divorved and rebuilding. The 1800na month here in WI feels like I should be paying that into a mortgage, but I dont want to live here past the job. I originally thought of buying in Bayview,  Milwaukee and either rent it out or sell it when the job is over. Not sure if that makes sense either. Im all over the place, and unsure. Ive already been working in this area for 1.5 years and we found out we will be working a few other phases which leads me to the 2-3 year mark

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  • Robert EllisBusiness Member
    Developer · Miami, FL · Member since 2014 · 3k+ posts · 1k+ votes
    3mo
    Quote from @Leti Salas:

    Hello,

    I'm in the market to buy my first home and start building my real estate portfolio.  Im currently working in Mount Pleasant,  WI.  Im paying 1800 a month in rent, as Im here during the week. I live in Chicago and my rent through a family member is 800. I go home weekends. Im not sure if I should buy a multi unit in Chicago and house hack in the 500-700k range or buy in WI in the 400k range and get rid of the rent here. Ill be working here about 2-3 years. Any advice is appreciated. 


    The sentence that stuck with me was "I'm divorced and rebuilding my life."

    I remember making a purchase after a big life change, and I caught myself trying to solve every problem with one property. I wanted it to be a home, a great rental, a retirement plan, and the perfect financial decision all at once. That pressure made every option feel wrong.

    What helped was asking a simpler question: "Five years from now, which property would I be happiest to still own?" Once I answered that honestly, the decision became a lot clearer.

    When you picture yourself five years from now, do you see yourself keeping that property as a long-term rental, or do you think you'll want the flexibility to sell and start fresh again?

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  • Wale LawalBusiness Member
    Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
    3mo

    @Leti Salas

    If you plan on being in Wisconsin over the next 2–3 years, then I would seriously look at purchasing the house where you currently live and paying $1,800 per month in rent. The whole concept of house hacking is best used when it helps you both financially and creates equity, and getting rid of this rent can go a long way towards doing both.

    Good luck!

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  • Jeff Roth
    Real Estate Consultant · Ann Arbor, MI · Member since 2022 · 463 posts · 253 votes
    3mo

    Hi Leti from Chicago, Illinois-

    Great question! You work in Wisconsin but live in Chicago. You are paying rent in both places and wonder if you should buy a property in Wisconsin or Chicago to eliminate your rent and build wealth.

    You might think about buying a place in Wisconsin as it is less expensive and where you say your rent is greater as you rent from family in Chicago.

    Then, saving on rent and building equity, you can plan to buy a property in Chicago where it is more expensive. Hopefully, you will have some positive cashflow from your investment property in Wisconsin to help with the rent in Chicago in the meantime.

    At some point in the not too distant future, you will have the rents you collect increasing and equity building.

    To Your Success!

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  • JV Kaufman
    Investor · Gulf Coast · Member since 2026 · 37 posts · 13 votes
    3mo

    Gosh, the answer is obvious to me. Purchase a property in either place that has the potential for an extra rental (Unit) like you're living in with your sister. It doesn't have to be that close. A garage apartment might work well. Something you can live with long term if you decide to stay. It's a golden opportunity. Questions welcome. 

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  • Marisa VoelkelBusiness Member
    Real Estate Broker · Janesville, WI · Member since 2022 · 10 posts · 9 votes
    3mo

    Hi Leti,

    The WI market is still really booming. Rental properties for all durations (short, mid and long) are in high demand. I personally have 4 units in 2 duplexes at the moment. In each case, one side is a mid term rental under furnished finder and the other is a long term rental. It's a great balance and we stall under lease. I just checked the MLS and the avg sold price for a SFH in Mt Pleasant/Racine is about $312K, and for a multi family, it is about 235K (all of those are in Racine btw). Taxes are better in WI and WI/IL have a reciprocity so no matter which state you work or live, you get to choose which state gets your income tax. If you want to chat more, feel free to contact me.

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  • Leti Salas
    OP
    Member since 2026 · 6 posts · 4 votes
    3mo

    Good morning, 

    Thank you for the feedback.  Im actually living downtown Racine. Im in Construction and we are building the data center in Mount Pleasant.  Ive been working here 17 months already, with plans for the next few phases. My thoughts originally were to purchase in either Racine, Mount Pleasant or Kenosha. I started venturing to Milwaukee some weekends and fell in love with Bayview. So my brain started working overload. I also wasn't sure if I just buy a condo for now, sell it after the job and buy my multi unit in Chicago. Honestly,  doesn't necessarily have to be in Chicago, but Ill probably continue my life there. Or who knows, maybe buy something in warmer climates as I start reaching retirement age. Im trying to utilize this opportunity to start my real estate portfolio.  

    1Reply
    • Shay NaborsBusiness Member
      Real Estate Broker · Milwaukee, WI · Member since 2020 · 8 posts · 4 votes
      3mo
      Quote from @Leti Salas:

      Good morning, 

      Thank you for the feedback.  Im actually living downtown Racine. Im in Construction and we are building the data center in Mount Pleasant.  Ive been working here 17 months already, with plans for the next few phases. My thoughts originally were to purchase in either Racine, Mount Pleasant or Kenosha. I started venturing to Milwaukee some weekends and fell in love with Bayview. So my brain started working overload. I also wasn't sure if I just buy a condo for now, sell it after the job and buy my multi unit in Chicago. Honestly,  doesn't necessarily have to be in Chicago, but Ill probably continue my life there. Or who knows, maybe buy something in warmer climates as I start reaching retirement age. Im trying to utilize this opportunity to start my real estate portfolio.  


       The $200-300k range is great for multifamilies in Milwaukee right now. You can find something largely turnkey (maybe needs cosmetic work like painting and such but doesnt not require tens of thousands) the rent potential is there and in this price range you can buy in appreciating neighborhoods.

      Many people talk about Racine for investments but the population is smaller, so less future tenants, and there are simply less properties avaialble daily making it highly competitive.

      I specialize in investment properties in the Racine/Milwaukee areas, feel free to text to talk more in-depth. Thanks

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  • Leti Salas
    OP
    Member since 2026 · 6 posts · 4 votes
    3mo

    Ive been listening to podcasts at work in real estate, stocks, retiring etc...Im trying to set myself up as Im rebuilding after my divorce, 8 years ago. I put myself through an electrical apprenticeship at a later age, and now Im in a position to start thinking about my future. One podcast I listen to recommended this forum to join others who are in real estate or investing. I thought this might a good platform to start.  

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  • Chris SeveneyBusiness Member
    Moderator
    Investor · VA · Member since 2015 · 21k+ posts · 19k+ votes
    3mo

    The first question I'd ask before anything else is: what happens in 2-3 years? If you're likely leaving Mount Pleasant, buying there is a significant risk. Real estate transaction costs alone, agent commissions, closing costs, carrying costs, typically run 8-10% round trip. If the market doesn't appreciate meaningfully, you're not breaking even, you're losing money. 

    The Chicago multi-unit angle is a much more interesting conversation.

    At $500-700k with a house hack structure, you're buying an asset in a market where you already have roots, likely have better market knowledge, and can see yourself long term. The rent from additional units offsets your carrying costs, and you're building equity in a city with real liquidity when you eventually sell or refi. The fact that your current Chicago rent is $800 through a family member actually makes this more compelling, not less. That's an artificially low cost of living subsidy you should be maximizing, not replacing.

    What I would do, keep the $800 Chicago situation as long as you can. Deploy capital where you have conviction and staying power.

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  • Leti Salas
    OP
    Member since 2026 · 6 posts · 4 votes
    3mo

    Hi Shay,

    I'm highly interested. Im loving Bayview so far. I might be reaching out to you soon...

    0Reply
  • Crystal SmithPro Member
    Moderator
    Real Estate Broker · Chicago, IL · Member since 2014 · 2k+ posts · 1k+ votes
    3mo
    Quote from @Leti Salas:

    Hello,

    I'm in the market to buy my first home and start building my real estate portfolio.  Im currently working in Mount Pleasant,  WI.  Im paying 1800 a month in rent, as Im here during the week. I live in Chicago and my rent through a family member is 800. I go home weekends. Im not sure if I should buy a multi unit in Chicago and house hack in the 500-700k range or buy in WI in the 400k range and get rid of the rent here. Ill be working here about 2-3 years. Any advice is appreciated. 


    This is a math problem, not a simple math problem but one none the less. To house hack a $500k–$700k multi-unit with a low-down-payment loan (like an FHA 3.5% or Conventional 5%), you must intend to live there as your primary residence. Lenders look at where your W-2 income is generated. If your full-time job is in Mount Pleasant (over 70 miles away) and you spend 5 days a week there, an underwriter may flag this unless your planning to commute to Wisconsin.

    If you buy in Chicago, you still have to pay that $1,800/month rent in Wisconsin for the next 2–3 years. unless you plan on commuting. Carrying a $500k+ mortgage in Chicago while paying $21,600 a year in Wisconsin rent is a cash flow disaster, even if your Chicago tenants cover a portion of the mortgage.

    It's my understanding the microsoft just spent a little over $3B to bring a datacenter on line in Mount Pleasant and are planning on a 2nd center. Now I hear good things and bad things about adding a datacenter to a community.  Assuming the good things there will be a increase in housing depand with the of tech workers, contractors,..... that will be employed there. So Mount Pleasant may provide you a better exit strategy when you leave after 2 to 3 years.

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  • Kamil Lysik
    Property Manager · Warsaw · Member since 2026 · 107 posts · 37 votes
    2mo

    Hi,
    If I were in your shoes, I’d lean toward buying based on your long-term goals rather than your temporary work location. Since you'll only be in Wisconsin for another 2–3 years, a house hack in Chicago could make more sense if that's where you ultimately want to build your portfolio. That said, make sure the numbers work—cash flow, financing, and your ability to manage the property are more important than simply avoiding rent. Run the numbers on both options, and let the investment fundamentals guide your decision. Good luck!

    Kamil



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

    Hey There @Leti Salas!  I'm a little late to your post, but thought I'd still chime in.

    Very tough question - probably best to work through some questions to see what makes the most sense.

    - Why are you moving in 2-3 years?

    - Where do you want to be long term after the 2-3 years?

    - Which option provides you the best quality of life?

    - What's your highest priority wealth generation or quality of life?

    Not sure what neighborhoods you are looking at in Chicago, but it's likely to be a better long-term investment.

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