Hi,I typically rent my 3-bedroom property through a short-term rental platform, but I was recently contacted by an insurance relocation company looking to place a family in temporary housing while work is done on their home.

Your situation presents a classic trade-off between long-term appreciation potential and short-term debt reduction.

If you want real numbers and insights, I have a ton of resources on that.Happy to answer any specific questions, but the short version?

So in short.

Seems to me there is only upside for them but no share in any downside if the unit is not leased to short term stay occupants.

But house hacking, short/long term rentals, new build/ mixed use developments and  live in flips all have my attention right now. 

I have experience handling this in Michigan with my short-term rental.

A lot of carry-overs that make it easier for us to understand the markets and pricing (the numbers tell a story).You may want to work to find a company that will bring you on as an LOA for a short time while you're getting licensed (and maybe they can help sponsor your testing). 

Are you looking for retirement in 10 years and an appreciating market or are you looking for a cash flow now maybe a short term rental or inexpensive cash flow market

Short answer: No, you don't need to (or likely want to) transfer the deed to an LLC before selling.