The only issue is the tenant. 

Each town/county may permit or ban short-term rentals differently across the city.If you DM me the address I can look it up for you.

I have had many work group bookings with no issues.

Houses there twice expensive that in Detroit and I can afford them, but the risk to buy poorly fixed flipper is seems too high(I've seen couple of bad flipped houses for sale, that had some issues with permits after fixes).Cleveland seems similar to Detroit.

It increases complexity and cost dramatically and thus should be avoided.Whether you need an LLC at all and other legal protection issues - now that indeed is for attorneys to answer.

This does not appear to be an issue for the tenants or the property maintenance (ie, no calls about tiles, soft floors, rot, etc).  

You do not want to have an issue with fair housing or the many JC regulatory agencies.

Rode it though some funky seller issues whereby it changed hands between 2 different owners while I had it in escrow (fun!).

Rode it though some funky seller issues whereby it changed hands between 2 different owners while I had it in escrow (fun!).

I don't see an issue with that if the tenant is willing.