SF Bay - California Coast down to Central America
There''s surely nothing wrong with your basic plan. But here''s the snag: yes, you really need more on-the-water experience and more time shopping (and scrounging in the bilges of) boats...but two years is hardly loads of time before you need to start using your own. In fact, two years is roughly the minimum time I''d recommend people give themselves to prep a boat before taking off to remote spots. This isn''t JUST to have the time to buy and install some equipment. How does she sail, in what conditions? How does the rig need to be modified (how about an inner stay for that 40 kt blow most folks will tell you is coming on your way south)? And out of the infinite # of choices, which gear do you most need that your budget can support? And after installing "stuff", shouldn''t it get a good shakedown - especially the important stuff like a vane (or autopilot), DC electrical system, and how full your tool box is?
We started looking at just the kind of trip you plan back in the mid-70''s and truthfully, it was easier to do so back then. E.g. a friend bought a Cal 34 - simple, good sailer, few systems, did well if the engine packed up - and took off for 6 months, had a ball, spent little beyond the base purchase price (which was also modest, even for that time) and he never knew he needed to worry about all these systems and choices. Moreover, if a time warp and allowed him to sail back up to San Diego today, he''d have a much better idea about which mods he truly needed vs. all the things that vendors, manufacturers, magazines and ''experts'' are pushing on someone in your shoes.
Get on the water, but also get reading and get shopping. Look for something in the 32-35'' range with a good rep, less than 10 years old, with few but quality systems, and BELOW the budget target you''ve set...and see what you find. I''d bet you''ll have multiple choices within 3 months that you''ll feel very good about.
Good luck to you!