I moved to Chicago in April 2021 for my girlfriends job. I work at a tech company in NYC. I don’t expect to live in Chicago for more than 2 more years. Is it dumb to purchase an apartment and then when I leave try to rent it out to people?

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I wouldn't want to be a landlord here vs. Other more landlord friendly jurisdictions. I live here but bought rental property in other states.

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Which cities would you recommend?

I became an accidental landlord around the housing bust of ‘08 and still own the property. My experience:
1. Consider condo fees and building special assessments as well as forecasted rents -you may lose money some years.
2. Screen your tenants and use your gut feelings. If need be, take your time finding a good tenant. Do a thorough background check and even interview past landlords if hesitant. I need condo board approval and have to give money to the board each time I get a new tenant, and they have to review the background checks, so this is even more critical.
3. Develop a good relationship with your tenant. Fix things when broken. Get them to trust you. I had a tenant for nine years because of that.
4. Don’t get too greedy on the rent. It’s easier to keep rent lower and have a tenant in the building long term.
5. Have a good handyman lined up through referrals. Even better if the building has someone to make repairs.

Hope this helps

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Absolutely not. As a life long chicago/Chicago area resident the city is headed for a rough few years. Many people moving out to the suburbs. Job market is not attractive, crime rate is high. I would say try to enjoy a couple summers in Chicago and move on with yourself

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Upper class suburbs that lean right and are anti renter. Lake county if I was going to do Illinois, but i am pretty anti-illinois. Im sick of the prop taxes and unfunded pension liabilities looming over us. I own properties in suburban Detroit and southeast Wisconsin which have high cap rate and favorable courts. I am sure I am in the minority. A majority of landlords who live in Chicago probably own property in Chicago. So I am sure there is a way, but too high risk for my taste. And like you, I don't want to get stuck here for life. I spend a lot of time at my properties maintaining them, which is fine since I can drive. If you are going back to NYC seems like it would be a big headache. You can hire property management company but that's a big hit to your cash flow. I have 1 duplex that pays for itself and pays my rent in Chicago. Other rental is slush fund on top of that.

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Property tax and hoa makes it tough to find deals. If you just want to build equity by renting out, it should be okay.

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