Nonstop flights and lots of them make commutes easy.

Connections to an airport served infrequently that commonly has weight restrictions, such as Key West, make commutes hard.

Depends on how much pain you want to put up with and where you end up based.

Something with a Miami base looks do-able. Atlanta would probably be ok. Anything else would be painful. And remember that bases change frequently, so what you have now might not be what you have in 6 months.