I would just add that you should also have a look at your local legislative website to have a look at what regulatory bills may be introduced and are working their way through the system.
Realtors aren’t going to know and even if they did, they aren’t going to tell you. They just want to make a sale.
For instance, if you were buying a place in rural Hawaii Island and searched for bills, you would be shocked to see that ALL new rentals in ag zones are going to be banned. That means unless you are in a resort area you will not be able to use it as a STR unless you can show proof of paying tax before January 2018 and have the permit that had been granderfathered in by the previous owner. No such permits have yet been issued, and the permit process for these granderfathered properties are estimated to take at least six months.
There are at least 26 new pieces of legislation being discused at the state level.
I would be willing to bet there are homes in the ag zones closing at this very moment where the new owners expect they can rent them out on Air or VRBO. They will be sorely disappointed.
And if you did take your chances and rent illegally, the state legislators are trying to pass legislation right now that would make it a class c felony to do so. Yes you would be tossed in the same bin as rapists and burglars if you dare open an Airbnb Dashboard and list your place.
Most big cities are introducing regulation, even if it’s still in progress.
Don’t take a chance, research regulations now.