The state has some congress members that are anti-STR as the state recently proposed a 15% tax in addition to the occupancy tax (so 15% tax beyond what hotels pay).  

Keep in mind, just legitimately maintaining the legal entities proposed in either option would likely cost more than the properties you mentioned would make you in a year.If you still want to pursue the matter, the approach is to learn which way you want to go.

Is the CPA up to date on tax reform and more specifically the proposed REG 199A released about two weeks ago?

With that, lending process generally involves submitting a proposal to be reviewed by bank board, who approves, denies, or lends conditional approval. 

I think I know most of the answers to the proposed question and do know that it will require the proper steps through a real estate attorney and/or CPA.  

I would recommend something else as what you're proposing removes your involvement but not the risk while increasing your cost for basic real estate transactions which will require representation by an attorney/CPA as Trustee.Fun, huh?

@Peter Sik Since you reached out to the roofer directly, they should be providing a proposal independent of any insurance claim. 

In the H.R. 3936, Built in America Act, it was proposed to extend the 100% bonus depreciation until January 1, 2027.

I am considering writing a proposal for my husband...

The proposed regs say that IRC Section 162 will determine what is a trade or business.