I have a good full time w2 job so coming up with a down payment is not an issue.

Would I have any issues with the insurance company in case something happens?

Ideally, I like a city that permits short-term rentals through an active law allowing them as opposed to permitting STRs through the lack of a law forbidding it. 

It is a bigger issue in the city because the housing stock is older and that means more lead paint.

At first I denied all these ppl but as I sit here with no prospects, wondering if allowing someone to rent out the space, sleep in the van at night would be an issue?

Area has no issues with finding tenants.

There is such a supply and demand issue in many markets that low rates will drive prices higher.

We do require the client to provide a certificate of insurance with us named as additionally insured, and copies of any STR permits etc.

Put in a set amount at set intervals to minimize losses from buying at imopportune times.Hello James,Thanks for taking the time to respond to my post here - it's at least comforting to know that my Chicago market area isn't the only area facing this issue to the extent it has been. 

From it raining a lot the night before the property going active which brought to light foundation issues hidden behind the pre-existing finished basement paneling.