In my experience, a property with multiple cottages and outbuildings can provide all kinds of creative strategies...some folks try short-term rentals or even specialized retreats if local regulations allow.

Building a relationship with local real estate attorneys or agents specializing in STRs in the area can save you headaches down the line. 

Sober living hasn't much of a foothold in NE GA from what I can tell, but there is a lot of need for traveling crews that work in specialized areas of the trades. 

One thing that stands out is that they all have specialized and focus on a niche. 

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

It speaks to "nothing special here", that's what it conveys. 

Trying to get myself out there but I know this is a really special community to be a part of.

From the little I know of San Antonio (I am a wholesaler who specializing in selling STRs nationwide) its not a super hot Airbnb market but the amount you expect for rent sounds pretty conservative. 

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Brent Mendanhall, director of special operations....wtf does that even mean?