All damage that has been done to our place has been done by AirBNB guest.

It's block by block. 

We are looking at a house on the West side of PCB and wondering everyones recommendations- would you choose a house- 2 blocks from beach with a golf cart- (I can link the VRBO for anyone to see) or go with a Townhouse in Horizon South.  

So, I am not sure how I would pursue damages and unpaid (2 months rent) if I wanted to.In hind site I should have kicked them out, but I didn't - lesson learnt.  

Very certain we overpaid, but it was a dire situation where the old one broke and had caused water damage and the tenant didn't notice for a month... 

These things are all stacked up on the same block and look absolutely awful, nothing close that resembles this market.

You are going to want to file a claim against Person B and hold Person B accountable for the damage.

While this isn't common, I have know people that bought their first rental and when tenant moved out, had caused close to $20k in damages and skipped town after one year of living in place.  

I offered a reply asking about damage to gutter.

This is not even considering any damage that could be done to the property during the ownership of the buyer.