A trust transfer allows for smoother estate planning, and if inherited after their passing, the land receives a step-up in basis, reducing future capital gains tax.Each method has pros and cons depending on their estate plans and your long-term goals.

Has anyone here been successful in permitting a conversion?

Greater chance for success versus another location. 

My son is working on his first SubTo real estate deal in Crawfordville, Florida, and I'm hoping to find someone in this community who can offer him some guidance and support.He's eager to learn and navigate this process successfully, but could really benefit from the expertise of someone with experience in SubTo transactions.

Nashville is a fantastic market with strong rental demand and long-term growth potential.

The one that's short term and don't cost me a lot to initiate/originate.

I have had a rental property for a short period here in CT and have sold it in 2017.

That being said, you cant really rent out your pool or finished basement to a Long term rental tenant, but you can with an ADU. 

Nonetheless, you can base the DSCR calculation on PadSplit rent (if there's a history of PadSplit income being produced) or short-mid-term market rent (an analysis done at the same time of appraisal).

What about refinancing  costs or what ever costs that occurs at the end of the loan term?