It has a reputed medical school, it is a popular Caribbean vacation spot too.

b) Is the reputation brand ruined worth risk gamble with business uncertainty harassment from city.c) How do I scale , dripping 1-2 RV each private lot over many cities local regulations ?

Any reputable broker will offer you training on the sales process, just pick the one that you can live with their commission split structure.

Have you spoken w/ a reputable lender yet?

Had to stretch to the very top of my budget, but it was in turn-key condition and the sellers were very accommodating, so virtually no fixing/cleaning expenses. 25% down, 30 years @ 3.25% interest rate (0.25 point) which is stellar for investment rates.Drove back out 30 days later to sign papers, get the keys and meet with a reputable property manager.

Some reputable home warranty companies absolutely will cover water heater repairs. 

Believe it or not, your reputation will soon follow you, especially if it is not a good reputation. 

Network with investment focused realtors in your areas of interest and if they are reputable they should have a good property management company to refer to you.

If a buyer is putting down 20% and is pre approve with a reputable lender there's no reason to take the cash offer.

You should do some additional research on them to find out if they are a reputable company.