Furling Main Sails
I don''t use a mainsail furling system so, in that sense, I can''t reply directly to your query. However, two thoughts leap to mind...
The first is how surprised I have been over the last 4 years, most of it while transiting the East Coast twice, offshore cruising in the Caribbean and while crossing the Atlantic, in how favorable have been the comments about mainsail furling. Especially with European systems such as those made by Selden, many owners have praised these systems without reservation. I didn''t get to listen to comments about performance and boat speed and such because, frankly, I think they are generally so afraid of going on deck and so appreciative of cranking a winch from the cockpit (or if going on deck, being able to crank something at the mast in 2 mins vs. pulling in a reef for perhaps 5 mins while dancing on the coachroof a bit) that performance as a consideration slides off into never-neverland. I honestly expected to hear more equivocating about furling main performance...and I haven''t. What I have seen are those (rare, I guess) cases where boats limp into harbors with their mainsail on deck (or torn apart) when the system didn''t work at all, jammed or couldn''t be fully furled, and where the trip ended up being longer (and more expensive) than expected. In truth, I''ve only seen 5 boats with this problem so far, out of many hundreds of boats...so I guess the odds are pretty good. But of course, the real question is whether this is one of those areas where you want to ''have odds''.
(BTW I''ve found that a conventionally reefed main can get pretty blown out in the leech over time, too. Any form of reefing is going to wear the sail unevenly. You''ll find in the Caribbean some boats never shake out a reef as they move up/down island, a guaranteed way to prematurely wear a sail, it seems to me).
My second thought relates to your description that "I am looking for cruising boat to take us to the Carribean, Centeral America, etc. And some offshore work." This can cover a LOT of ground and refer to some very different circumstances. E.g. sailing the Thorny path down to the Eastern Caribbean, and then perhaps across via the Greater Antilles to the Bay Is., up the Rio and then N thru the Yucatan Channel, I would not consider a mainsail furling system the ''deal breaker'' that Jeff mentions. The runs can be done in short stretches, there''s readily available wx f''cast info available thru-out that area, plenty of hidey holes inbetween, and in truth the wx is usually pretty manageable - rarely more than 30 kts sustained. OTOH if I were e.g. considering a run across the bottom of the Caribbean (VZ-Columbia-Panama) or running down the W coast of Central America from Z Town, I''d have a real worry about that kind of gear, because the winds can be truly horrendous on occasion, due to funneling effects off the Andes or thru the Central American backbone''s gaps, respectively. So...perhaps another issue to sort out is just where you hope to be going - specifically, and in which seasons - and what the implications might be for those waters.
Good luck; you''ve got a lot of fun headed your way!