I'm going to propose that to him writing today.

Why is this proposed?

I'll throw it out there as an option, knowing that no one is really going to take it.Your proposed transaction is low leverage, so very good terms should be available, but FDRs New Deal in the 1930s (which created the kid-friendly home loan ecosystem -- home loans commonly had 10 year balloon payments before that, even if you put 50% down) was only for homes, not for CRE.

Pay attention to the changes being proposed to the County's STR ordinance.

The proposed real estate investment is too broad for you to compare returns between the two, what is the purchase price, what kind of repairs do you need, what kind of rent are you going to get, what is a good estimate for appreciation on the deal. 

@David Smith I was lucky enough to get a proposal from TV host on spike TVs to handle operations via a management contract.

I am hopeful that someone can propose an innovative strategy around my challenge.

Borrower Experience: make sure your borrower has experience with the strategy they are proposing.

I am looking at buying a distressed 1/1 coondo and turning it into a 30 day rental, and am about to write my proposal. 

Your proposed plan is a good option.