Larger cities offer better infrastructure, such as international airports, interstate highways, and a broader talent pool, making them attractive to businesses and tenants.Avoid Rent ControlRent control laws can hinder your ability to adjust rents to match inflation, limit tenant screening, and complicate evictions.

The government of Costa Rica has a policy to limit development and doesn't invest much in infrastructure to bring tourism.

Surround yourself with knowledgeable professionals who can support your real estate endeavors.

Many of the surrounding communitie are up and coming with a lot of developments happening. 

We have extended our search to the surrounding counties outside of Pinellas at this point but would appreciate the opportunity to run numbers by you for a second look.

Quote from @Brendan Jones: For the homes, and or properties that you will use as a primary or a rental property one big thing I look for is infrastructure in the area, extrinsic value (I.e. hospitals in the area, schools, and job market), and the last thing is creature comforts for people (I.e. is a store to get groceries 1 hour away or 2 minutes away).

I'm not in that market so I can't speak specifically to it, but to me the deciding factor would be what the surrounding units and area has. 

I look at so many properties, chances are I have been inside some of the surrounding properties already.

Residential subdivisions, while potentially less complex, can be hit-or-miss depending on local housing trends and the cost of infrastructure development. 

Has it been in surrounding areas, OOS investing, or have you found deals in NYC?