Getting based in ewr is probably your best bet. You can take the tri rail to pbi fll or mia and as someone said earlier a shuttle from lga or jfk is $15 if you're unable to fly directly into ewr. I live in sfl and haven't really had problems getting to or from ord, iah has proven to be more difficult (the few times I've tried at least). Msp and dtw are terrible commutes from sfl.

How often you're home depends on the reserve rules and schedules on where ever you decide to go.

Hope this helps!