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.

I have text in my lease stating that the tenant is not allowed to make repairs to holes in walls and that any repair work that takes over 30 minutes or is larger than the size of small nail will be repaired by the landlord's hired labor at a cost of $30 per hour plus material costs. 

If it hasn't been stated yet, how about an escrow type situation for the money? 

LLC, incorporated, etc and also what state you are in.

Since you're a citizen but you live and work abroad you'd still qualify mostly for second homes occupancy or investor non owner occupancy (primary is hard to claim if your job requires you to be physically next to the office as an example so an underwriter isnt going to readily believe you unless you can get HR to write you a letter to state you're remotely capable of earning this income/job duties anywhere).Hopefully that helps let me know if you have further questions into mortgage planning.

It has limited new construction, low property taxes, and no state income tax.

Do that for six months while you save more before making a decision on what to do, especially on doing it out-of-state.

Perhaps it is hard for people from the states to understand - but the rule of law, and clarity in regulations etc really makes it so much more attractive than other places where you never know what new policies might come into effect forcing you to take massive loses etc.

Estimated CostsADU costs can range DRAMATICALLY depending on the state of the lot, custom vs fast track plans, size of ADU, materials and finishes, speed and quality of the builder, etc.

Not sure where Ana, but every state as you know is different.