If you had time, money and no job... WWYD

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If you had time, money and no job... WWYD

Luke Sirois
Member since 2026 · 4 posts · 0 votes

I have about a year until I return to employment and access to a substantial amount of money (borrowed privately). 

I would like to begin real estate investing, I rent currently and will be renting for the next 2-2.5 months. 
 
My plan was to do sober living through a rented property, and if I like it I could buy and run it out of my own place. The attraction I have to this is the component of helping people combined with fast returns (These types of businesses can break even in 2-3 months if ran lean and renting). An issue I have run into is that no landlord is interested in allowing someone who has never owned a sober living home to operate one out of their house. The ones who are interested tend to be desperate for good reason (D class neighborhoods, deep south side). 

So, I beg the question. If you had the time and money, what would you do?

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Jules Aton
MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
4mo

Just my opinion but that is a hard crowd to manage. SUD comes with likely high relapse rates 40-50% from NIDA I believe? And activities that may involve illegal things and sometimes death in or around your property. Not in any way saying it isn't a worthwhile venture that can be lifechanging for some but not an endeaver that has any appeal for me. If I had time and money and needed something to keep me occupied I'd probably do STR or LTR house hack tri or four plex. Both should keep you busy in a property with less risk overall.

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  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    4mo

    Just my opinion but that is a hard crowd to manage. SUD comes with likely high relapse rates 40-50% from NIDA I believe? And activities that may involve illegal things and sometimes death in or around your property. Not in any way saying it isn't a worthwhile venture that can be lifechanging for some but not an endeaver that has any appeal for me. If I had time and money and needed something to keep me occupied I'd probably do STR or LTR house hack tri or four plex. Both should keep you busy in a property with less risk overall.

    1Reply
  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 968 votes
    4mo
    Quote from @Luke Sirois:

    I have about a year until I return to employment and access to a substantial amount of money (borrowed privately). 

    I would like to begin real estate investing, I rent currently and will be renting for the next 2-2.5 months. 
     
    My plan was to do sober living through a rented property, and if I like it I could buy and run it out of my own place. The attraction I have to this is the component of helping people combined with fast returns (These types of businesses can break even in 2-3 months if ran lean and renting). An issue I have run into is that no landlord is interested in allowing someone who has never owned a sober living home to operate one out of their house. The ones who are interested tend to be desperate for good reason (D class neighborhoods, deep south side). 

    So, I beg the question. If you had the time and money, what would you do?


    If I had the time, access to capital, and no job tying me down, I'd focus on building a scalable real estate business rather than chasing the fastest return. Sober living can be rewarding, but it's also an operating business with regulatory, management, and tenant challenges. Personally, I'd spend that year learning a market inside and out, building relationships, and acquiring cash-flowing rentals or small multifamily properties. If you're open to out-of-state investing, some Midwest markets still offer opportunities where the numbers make sense without needing a highly specialized business model. The goal wouldn't be to hit a home run on one deal, it would be to create a repeatable system that can keep growing long after that year is over.
    [email protected]614-418-6081
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  • Chris SeveneyBusiness Member
    Moderator
    Investor · VA · Member since 2015 · 21k+ posts · 19k+ votes
    4mo

    I would be doing what I am doing now - which is buying and selling mortgage loans. I would probably also do some development projects as I spent 20+ years in construction and development as well. 

    Do what you love but also what you know how to do, as the last thing you want to do is lose all the funds. 

    7e investments53 Reviews
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  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    4mo

    Welcome Luke! I'd first encourage you to go to all the local meetups you can in Chicago. There's a great community. My favorites are Chicago multifamily club and cash flow breakfast club currently. 

    I would also listen to the straight up Chicago investor.

    If I had time, access to capital, and no job, I'd probably be looking to flip and brrrr properties if I had the team to do so. Otherwise, I'd probably consider being a real estate agent or wholesaler or leasing agent depending on desire and then try to invest on the side. 

    For me personally, given I do have time constraints, I prefer buy and hold real estate, specifically house hacking. 

    [email protected]
    Brick House CPAs53 Reviews
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  • Victor SoBusiness Member
    Real Estate Agent · Chicago, IL · Member since 2017 · 325 posts · 193 votes
    4mo
    Quote from @Luke Sirois:

    I have about a year until I return to employment and access to a substantial amount of money (borrowed privately). 

    I would like to begin real estate investing, I rent currently and will be renting for the next 2-2.5 months. 
     
    My plan was to do sober living through a rented property, and if I like it I could buy and run it out of my own place. The attraction I have to this is the component of helping people combined with fast returns (These types of businesses can break even in 2-3 months if ran lean and renting). An issue I have run into is that no landlord is interested in allowing someone who has never owned a sober living home to operate one out of their house. The ones who are interested tend to be desperate for good reason (D class neighborhoods, deep south side). 

    So, I beg the question. If you had the time and money, what would you do?

    I would Househack a 4 unit property. You can get in with only 5% down and you’ll gain much insight on how to be a landlord, what the landlord/tenants laws are, etc. If you have money leftover, you can invest in other things. 
    Victor So Real Estate LLC517 Reviews
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    1Reply
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