A new construction loan Might be more difficult to qualify for than an existing structure loan.

I think a more appropriate question to get a better quote1) Instead of doors, it should be properties.If you are okay with tracking by the overall property.If you also want further tracking by unit, it would be more work and likely a larger bill.2) How many Accounts do you have(Bank Accounts, Credit Cards and mortgages)3) How many transactions do you have per account, 50 transactions will take more time/work than an 5 monthly transactions.

It protects it from outside liability (let's say you drive recklessly and kill someone, and your personal car insurance gets exhausted, the suing parties cannot come after the rental property because it is not personally owned by you). 

The cash flow to LL using PM for STR is not substantially different after including extra expenses than an LTR.  

I truthfully don't see a great deal of negotiation leverage as this building is the norm  rather than an outlier fact pattern.

 But to be fair, besides people not being happy with those kinds of houses anymore, builders couldn't build them and make any money due to high costs of planning, permitting, sewer and water hook ups, electric hook ups, etc.Well, we do have this Tiny House fad right now, but can someone explain to me how these are any better than an old fashioned trailer?  

If they are so stubborn or shortsighted to see they get more this way than an outright sale, then just do a normal outright sale.

Want to work more than an hour a month and I believe he saves me more than he costs. 

It may work and if it does it will be cheaper than an eviction.  

https://www.courts.state.co.us/userfiles/file/Court_Probation/18th_Judicial_District/18th_Courts/Eviction%20Plaintiff(1).pdfSo forcible detainer is the step after the Writ of restitution is signed by a judge and it is even worse than an eviction record on file.