Thought I would update for anyone else in similar shoes. I ended up going with Island Birds. The three of us are good to go on the small Piper Aztec. According to the reservation we can bring 75-100lbs of baggage each (not happening)

Booking was dead simple and response times to everything, including my original inquiry were swift. The instructions said to be at the Island Birds lounge on the top floor of the Jet Blue terminal 30 minutes prior to our scheduled departure. I assume the elevator they reference, left of all the check in counters, is prior to any checkpoint/security screening so that should be no problem.

Thanks to all for the input.