It did need some upgrades, but I'm definitely out of pocket a lot on this one to turn it back into an STR. 

Most definitely @Jerryian Francois!

Your approach here has definitely given me a lot to think about in terms of spotting hidden value.Curious, with the deferred maintenance challenges you faced, was there anything unexpected that came up during the rehab that you’d approach differently next time?

. :) Yeah, definitely a recording.

@Marc Shin, Soundproofing is definitely something worth tackling for a short-term rental—it’ll keep your guests happy and help you avoid complaints.

It's definitely possible to get a loan as a foreigner but the rates will be high(er) and the downpayment required will be as well.

These will be LTRs and I will most definitely be playing the long game with these.In addition, as rates go down in the future (hopefully) I plan to refinance as most of us do.

@Jacob Dalton, I'm going to have to agree with Jonathan Klemm (sorry, couldn't tag you) & @Brie Schmidt -- you can definitely be a successful landlord in Chicago with the right team in place.  1000's of investors do it every day. 

Definitely screen properly and don’t cut corners!

Strategy you are talking about it definitely something can be done.