I guess I have been hesitant to bombard people with the same message three times.

I would go with "3) get a structural engineer to "stamp" it and say that it's up to code" Can you imagine what you'd be in for if someone died in an un-permitted bedroom when you have knowledge and have been notified by the city?

This is an area of a lot of ex-pats and longtime vacation takers, or people that have rentals there.

I've done this with my properties because I'm well known in my small town and don't want people to know what I own.LEGAL PROTECTION: By placing your assets in an LLC, you are legally separating them from your personal assets.

The concerned neighbor requested us to do something to put an end to the endless stream of unsavory people coming and going from that rental, with the main tenant in the middle of all of it.

This is far from impossible and many people have a lot of success managing their own STR, but it sounds more involved than what you're looking for.

How many will you sleep (more people a little more in monthly utilities).

That's how people get over-leveraged and into trouble.If you want to invest, do it the old-fashioned way: increase earnings, reduce expenses, save, then invest.

Actually the people telling me I can’t use B2 comps is Tax Shield!  

Also $0 claims always impact peoples insurance as it changes their "insurance score".