If the existing ceiling paint is damaged, the ceiling must be scraped, repaired and painted.

That doesn't exist folks.

Given your strong credit, rental experience, and the equity in your existing properties, you’d likely have some solid options. 

So there are now 20+ people to connect with in order to get a clean marketable title, (none of these existing family members have any idea of the property even existing).

We typically buy existing debt but still good to know. 

Deregulation Push: Streamlining housing development regulations and approval processes2.

•Local Regulations: Are there any important rules, taxes, or permit requirements for STRs in Gulf Shores that I should be aware of?

You familiar with development/building regulations in Ontario? 

There are less lenders that do this but they exist.

The seller will have reduced debt capacity because the existing note is still calculated as a debt - they MAY be able to include an offset equal to the buyer payments after a period of time, BUT often the seller is surprised to find they can not qualify to purchase another property3.