It's worth mentioning the STR regulations are relatively new, and I think some properties currently operating are basically grand-fathered with the old permit, and I don't know if being a new owner one'd be able to get a new permit if it's not in the designated location.

STR regulations have been a VERY hot topic here for the last year (and even beforehand).

With high price per door and high rates, you wont find any cash flow.STR market is also very saturated and we're seeing more regulation there.I'd keep the end goal bigger multifamily deals.

Big cities tend to have more regulations, more crime, more leftist-leaning policies that hurt investors and private property rights, etc.

However, private financing options are becoming increasingly popular for scaling portfolios.Zoning and restrictions: As you mentioned, regulations for short-term rentals, such as Airbnb, vary significantly.

Ensure you understand local regulations regarding permits; it’s usually a good idea for your associates to form an LLC for liability protection, but individuals can do renovations as long as they pull the necessary permits.

There are markets that have built in "gotchas" like the rising cost of insurance in coastal FL, regulations in much of the west coast states and property taxes in Texas; however, the deal itself is the most critical factor.

Short-term rentals like Airbnb can perform well in tourist-heavy areas like Vegas, but be sure to check local regulations.

Real estate agents are not highly regulated in Costa Rica as opposed to North America.  

Also check if there are any boarding house regulations in your area that would impact you.