Wanting to go offshore in 2 yrs - buy right boat now ?
A couple of add''l thoughts...
1. If you haven''t already, you might consider visiting www.searoom.com and correspond with Alec Main. He & his wife circumnavigated on a Prout 33 and there is also info on their own website (from her book on the trip) about the boat that is quite positive & detailed. You can find their book/website info at searoom. Also, keep in mind that Alec would not choose a Prout 33 now, given what they know - wants more bridgedeck clearance & sail area - but he remains convinced it was a good choice.
2. For your planned travels - out & about the Caribbean - you''ll find almost any kind of good/bad wood/steel/fiberglass/ferro boat out there, doing it and not taking much of a risk. I''m currently in Trinidad having made the passage in a Pearson (which is just another ''price boat'', not built with extended offshore cruising in mind) and it along with its many peers are sufficiently capable IMO.
3. Therefore, I believe it''s more important you shop for an adequately built boat that''s been well equipped and maintained. This is in contrast to the oft-offered advice that one shops for an older but offshore-intended boat that comes with other issues. You''ll find the latter type of boat, while fundamentally stronger than price boats, could cost more in the end (to update the gear, or otherwise overcome the higher initial price).
4. For mere mortals, economically speaking, arguably THE most important gear you need to make sure is aboard and in top condition is either Marine SSB or a ham SSB rig. I say this because weather is your only real issue given today''s GPS tools and the short (2-4 day) hops you need to make.
5. Be advised that, at least at this time as best I can determine, Costa Rica is is usually not fully covered by U.S. insurance carriers. If coverage is offered, it will omit some of the most common losses that motivate you to carry insurance in the first place (theft, boarding-related damage, etc.). The same is true for Nicarauga, Columbia, Cuba, Haiti & often much of Panama.
If you''re thinking of doing the Carib 1500 or otherwise taking the boat in a more direct routing, much of my advice is inappropriate.