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

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...

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.

Are you offering any special programs, incentives, or advice to help them close out the year successfully? 

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

I am expanding to more specialized Airbnb this year.

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.

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.

I think what you’re referring to is a checkbook IRA so you can bypass the custodian when performing transactions/investing and all assets/accounts will be held in the name of a special purpose LLC or Trust which is the instrument that gives you checkbook control.