you dont a good agent repping a buyer is going to go to bat for them not U keep in mind many sellers lie about all sorts of things.. not saying your that way but it is common the industry.

Am I potentially exposing myself to some sort of issue here?  

It's a free market, no body can force anybody to buy or sell anything.

It ended up getting sorted out and the rent got issued through the CHMA, but there WAS a delay.

I have a CPA I work with who I’m sure will sort all of it out, just didn’t want to do something if it would cause a huge tax headache later.Do you know if you convert a STR to a LTR after a cost seg, will it cause a large repayment of taxes (I’m doing the cost segs to lower my W2 tax rate).

All sorts of little things you know if you are local but hard for outsiders to navigate. 

I think a free market would sort this kind of thing in a very efficient manner. 

When repairing an existing home, there always seems to be some sort of a surprise... termites, underground plumbing, lots of wood-rot under the shingles, you name it... 

My priorities are cash flow and tax benefits, and I’m looking at purchasing a 2/2 that fits up to 10 and is along a body of water.

Most areas we have found that are hot spots have some sort of quasi "local" booking entity, we try to belong to them as well if they are credible.As in anything with being in business almost 25 years, the better your relationships the better the response, this is no different.