Essentially, this boundary delineates the city limits of Lexington and regulates new building developments within its confines, preserving the surrounding rural, natural, and agricultural landscapes.

You can't move forward on ANY strategy until you know what regulations are going to apply to your property.

All logic tells us that either the SEC or CFTC will govern those trades and ALL will have to be compliant with the regulations of either agency. 

If you're open to a bit of creativity and local regulations permit, converting additional spaces like garages into rooms can further enhance your rental income.Overall, your strategy has a good direction.

This reminds me of how I view STR regulations in Colorado.

It’s just not smart.Second, with an FHA loan, any title company that handles the subto transaction is ignorant of the regulations/published guidance which forbid it. 

Depending upon whether they are a bank or a trust company, custodians are heavily regulated by the IRS, DOL, possibly the FDIC, State Banking Commissioner, and the Comptroller of the Currency.

We were initially told that this would not be possible due to regulation.

What are you thoughts on STR changing local regulations? 

Forming a Homeowners Association is a good idea, but can a HOA legally enforce rules and regulations on neighbors who do not comply?