Does the building have central air?

Possible his drone showed the most evident damage and not so much like being on the roof.

But if you are able to risk the money without damaging yourself financially and it's truly your passion, then sure. 

Last year, a heavy rain and storm damaged it and I had to replace the entire roof which costed me $21K. 

I am launching my first STR and I was wandering what are the most common site for bookings besides Air b n b and what are their pros and cons. 

., major structural termite damage, small mold issue).

If the later is the case, unless your contract with that buyer had specific performance language in it, there is nothing you can do.As to the advice above about potentially clouding title, you are now entering the legal realm and you should NOT be taking legal advice from anyone other than your attorney as clouding title in THIS case can swing back at you from the original sellers for not performing and claiming damages against you.If you intend to wholesale, you need to do it legally and ethically and in many states, that requires either a license, closing on it with your funds or borrowed funds, then marketing for resale once you have title, or having your buyer upfront, forming a legal entity with both you and buyer as owners.

I own rental properties in one city and two of them had insurance claims in the last 2 years due to hail and tree damage.

In that case, if they can provide us with proof of contract cancelation, we terminate their lease without a fee and refund their full deposit (assuming there isn't any property damage).

Studies have shown that the longer a poorly paying or non payment tenant stays in a property, the greater the chance they do purposeful significant damage to the property.