Investing in a 2nd apartment rental in Chicago?

[Chris132]

Hey all!
I rent out my 1-bedroom in Chicago - Wrigleyville to be specific. I am thinking about investing (security deposit, 1st and last month's rent) in a second apartment to rent out around Chicago. Wondering if anyone is in a two apartment rental situation already and if you have some advice for me!
Best,
Chris

[Guillem2]

we did that and it worked very well for one season. then we got a winter renter just to cover costs, waiting for the next summer season. apparently a neighbor of the landlord complained about noise and we lost everything..... all furnishings, art works, appliances, etc and our security deposit naturally. we didn´t lose money, net, but a ton of work to get the place up to Airbnb standards and then we lost it. be super vigilant...

[Toni21]

I do this now so I can live in my sons school neighborhood. I started with a studio and now I have a studio and one bed. Currently flipping the one bed so o can make more profit.

Lots of laundry!!!!