Jeanneau 37, Great Lakes to the Caribbean?
Well...I''d agree that she isn''t the ideal boat for extended cruising, there certainly are lots like her down in the caribbean and they all got there somehow!
I''d suggest that she is well suited to short coastal passages and ICW work and can easily cross the stream to the Bahamas. From there you can follow the "thornless path" down to the Carib with nothing more than overnight passages in settled weather if you have patience and no timetable. (see Bruce Van Sant''s guide for specifics).
Of course you''ll want to equip the boat for extended live-aboard life but I wouldn''t put a lot into trying to "beef her up". For me, the essentials for long term live aboard are:
1. An oversized anchor and all chain rode on a windlass. (backup hook and rode required as well.)
2. A reliable electrical system capable of charging an expanded battery bank...generator or wind generator/solar
3. SSB/Weather Fax system for Carib...not necessary for East Coast or Bahamas.
4.Appropriate safety equipment..EPIRB,Raft,Sling,Jacklines etc.,Rig cutter
5.Complete set of engine spares,pump spares and hose spares.
There''s lots more to it, but those are the essentials from my perspective and your Jenneau is certainly capable of handling this type of fit out.