Managing a short-term rental (STR) can feel like a full-time job.

If you're in one of the Primo in-town neighborhoods your rent floor should be higher.Compared to short term rental - your gross rents will be lower, but that comes with lower headache. 

Hey everyone, Has anyone done short term rentals in Chicago.

We tore down half the home and saved 400 sqft, turned into a tiny home short term rental.

Are there any markets you would recommend for long distance investing?

Being from Chicago, I'd tend to agree with you @Craig Jones those areas of Wisconson and & Michigan are driveable from a lot of those metro areas you mentioned, but I think the toughest part of any northern short term rental is the seasonaility. 

Read "Long-Distance Real Estate Investing" by David Greene and follow him on the David Greene podcast.

After minor renovations to enhance its appeal, it has consistently performed well on the short-term rental market, particularly on Airbnb, where it maintains a high 90% occupancy rate.

Mid-term rentals could be a sweet spot between short and long term depending on where you are and what your market looks like.

Video is even better, if professionally done.Most of our travelers that are coming from any distance are happy enough for great pictures and good customer service to rent.