Quote from @Makani Donaldson: From what I understand, different islands or cities have different rules, and they are getting stricter.

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

I didn't have much money, and not much experience but I used my background in finance to put together a syndication and buy an old office building and drive thru on .59 acres with the purpose of developing housing.My passion was creating housing in a city with under 2% vacancy and skyrocketing housing costs.

It’s my favorite city in Florida! 

If that isn't satisfactory speaking at a city counsel meeting about the subject would also seem appropriate. 

This was a no money down deal was a tri-plex, duplex, SFR and studio all on a few city lots.

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I navigate through cities and towns, identifying areas that are both friendly and challenging for STRs.

I imagine there is a good level of demand for your services in a city like Nashville!

I would like to know how to read the market a lot better and learn how I can see wether or not a certain city is thriving or not, if where I purchase the duplex is thriving I'll just settle there and target SFH's there instead of moving out of state.