A slow leak has caused $2.5K damage to a rental property of mine.

If I am going to the more affordable area, I'd try to stay within a block of Kensington Ave versus further in, if that makes sense.I've spoke to some PM's in the area, anything specific you're referring to? 

I believe this may have been passed down to them prior and they don’t really do this often based on the condition of the home, and lack of communication.The back yard is overgrown with weeds, the sidewalk has been damaged and rubble for years now.

The seller has an obligation to minimize his damages, but he might be able to sue for the difference after he closes on the contract with the person whose word is good.

I recently put my Pensacola house up for rent on Zillow, and I received an email from a company that specializes in temporarily relocating families displaced by damages to their home.

They did a lot of damage.

Do you find someone on places like craigslist to get "boots on the ground" to look at the property and assess any damage?

I would ignore/block those emails, if I were you.

Louis is indeed block by block

If I am not mistaken the current rule is a 12% STR "occupancy" on a given block face in Bexar county.