HAM and SSB
You might look into the Waterway Radio & Cruising Club, which meets daily all year at 7.268 LSB beginning at 0745 eastern. If you choose to join (not needed to use the Net or meet the great people) for a small fee, you will receive newsletters and a directory of boat-owning/cruising hams who are a huge talent pool and who sponsor a variety of events & services. These members live all along the Gulf and East Coasts of the U.S. and their email & phone #s are in the directory. A brief scan will probably produce neighbors who''ve been doing what you''re thinking of. For more info, visit http://www.jstorm.com/wrcc/
The best choice for cruising seems to be a rig that can handle Marine SSB and Ham bands, as somewhat unique services and Nets are handled in both frequency domains. I would encourage you NOT to offload your older, less powerful rig automatically, as power isn''t as important in a good SSB installation as the antenna & counterpoise...plus all-around excellent wiring. But having said that, Winlink (the Ham email system, but also oh-so much more) is the best non-commercial offshore email system available today and is totally free to hams, provided your radio is capable of handling the traffic and you''ve purchased a TNC for about $500 that allows analaog radio signals to be used digitally by a laptop.