Good posts... thanks guys!
Since most likely I will be sailing solo, I have to keep that in mind as well... small is beautiful when you are alone. I'm used to camping in my 20 foot Mirage, on top of a layer of gear and supplies. Money is definitely an issue but I want a solid boat that is already in good shape when it comes to all the important components - it costs way too much money to re-do all of them. Much cheaper to buy a boat that already has what you need.
This boat caught my eye because it is on a trailer and I can store it at home inland until I'm ready for the big trip (in about 2 years).
Would you think this CD26 is safe enough for the Mona Passage and a Caribbean cruise all the way? This is stage 2 of my long term plans.
I think just about any of the Cape Dory boats will take you anywhere you want to go. Our 27 has been at least as far as the BVIs and has made the Mona Passage, but she was at the hands of someone that was very experienced. Now she's in the hands of a few morons :P Any of the Cape Dory boats are capable, it's more a matter of your skill. You can search the CDSOA boards and find people that have made fairly significant passages in almost all the boats.
As for this 26, I'd feel rotten buying her in the shape she's in and letting her sit in the back yard for 2 years. That seems like a real shame, considering she's ready to sail as is. I know you said you didn't want a project, but why not spend less on the acquisition and outfit her the way you want across the 2 year period? It seems like a shame to take a seaworthy and ready boat out of the water for 2 years to sit, especially for that kind of $$. You may end up shelling out a little more $$ to fixup the project, but provided it's nothing serious, I doubt you'd be investing a lot more. Our CD27 has definitely been a project and we've paid more to get her up to shape than we could have if we bought one already in good condition, but we learned a LOT about the boat, have all new components in her, and know just about everything backwards and forwards about her components. I spent more doing it, but the experience was worth it. The benefit of this will probably vary on your experience level, though. I just hate to see a boat like that sitting
Given your requirements, I'd seriously consider a Flicka 20 as well, especially if it's just you.