@Mark AndersonFirstly, I’m located in upstate New York, and am not sure of your local laws and regulations.

., We have a lockbox hanging off the propane regulator on the back of the house.

I assume that it is more tricky with regulations and simply having a greater number of tenants, but I just wanted to get some opinions.

I am located in BC, Canada, I understand regulations will be somewhat localized. 

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 ?

Arvada and Littleton are going to be your outliers that allow STRs, Arvada passing regulation allowing it and Littleton doesn't currently have specifics saying "no" which could change in the future.Sounds like you will be renting the place out long term, so be sure to lease for a minimum of 30 days out this way if not in the above markets!

Right now you may or may not be able to evict someone due to the moratorium, so calculate how that works into the plan.Now with all the negatives, you may be able to rent it and collect rent month to month during any hold period if you get the deed to the property.Just some things to research and think about....every state is different as to they handle these sales....and the rules and regulations on them.It's just not as easy and profitable I think in most cases in most parts of the country as your example.

Hi @Jacob Temple, The tax code and regulations do not have any "holding period" required. 

Also, be sure to check local rules and regulations, it seems like Hawaii isn't very friendly to STRs overall. 

Look at the u regulated TX Power and also home construction standards.