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.

Right now, land (unless in a hot market) takes a special type of buyer/developer to turn it into money, so you're better off finding the thing the people with the money want. land tends to sit a long time...

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

I do specialize in VA loans, am licensed in WA, and would be happy to help you out at least with advice.

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.

Found this off-market deal through a local wholesaler specializing in distressed properties.

Found this off-market deal through a local wholesaler specializing in distressed properties.

Without writing a book, google these two terms.Zombie CondoHOA Special AssessmentThen search for news on condos in Florida from this year.

Find an architect who specializes in this type of work, and who is very familiar  with the building department

Eric, First, Good idea on searching for a realtor specializing in STRs.