Yes, we can all agree there’s historic vacation communities where STRs have an informal historic precedent or maintain a supply/demand advantage that makes regulation unattractive to local municipalities, but there’s plenty of others where the investors have overbought, managed properties poorly, and are now part of a perception problem that’s driving bad legislation atop stupid headlines of irresponsible investors who think they’re operating in an ATM industry versus hospitality. 

The 2024 legislative session just ended with nothing. 

It will be interesting to see what happens with the pending legislation related to bonus depreciation (passed the House and in Senate). 

Asset Protection: Take into account the degree of asset protection offered by state legislation.

Borrowers have to pay their HOA I am not from Florida either but I believe most states allow the HOA to foreclose for non payment of dues most states give HOA's special foreclosure laws that are stronger than a simple lien in order to give the bank 1st priority otherwise an HOA is a document recorded prior to the first and would hold priority if they didn't sign it or legislate that position away.

As Russell and Wayne correctly pointed out, if the wholesaler did not possess the license, and this transaction falls within the legislation's intent there's nothing more you can do.

As @Stuart Udis mentioned, definitely make sure local zoning, legislation, use, etc allows for short term rental space.

I want to make sure I'm acting in accordance with the local government's legislation, but I'm having trouble making sense of all of the information I'm finding on https://www.roanokeva.gov/.How do investors usually navigate legislation requirements when starting renting in a new city?

 In case no one else posted, this is what Cali is up to.
https://www.mercurynews.com/2024/02/29/paw-friendly-proposed...

It was pretty hard to find properties where the numbers and landlord laws made sense which is what ultimately led me to investing in Columbus, OH.Not to mention the upcoming legislation on the November ballot that can really hinder your returns from rental properties.