Wanting to go offshore in 2 yrs - buy right boat now ?
I think you need to offer more info in order to get truly useful info. You talk about your cruising plans in relatively definite terms, but to where? Some view trips up/down the ICW as cruising, which it is, while others think of it in terms of Oz, Kiwiland and a circumnavigation.
Similarly, you mention being away from sailing for 5 years. If that was after 20 years of competitive racing, so what? If it was after dabbling for a few years, there''s a generally huge learning curve you need to climb, if long-term cruising is your game.
Finally, my sense of it (after 4 boats, 3 extended cruises and a TON of stuff I still don''t have a clue about...) is that ''sailing'' is a very teeny part of ''cruising''. Cruising is about logistics (from mail to finances to a thoughtful itinerary that finds you prepared to truly enjoy where you go), about a wide and sometimes depressingly deep need for skills (engine, pumps, navigation, etc.), and many other things that fall outside of knowing how to sail a boat...let alone, well.
Shoot some more specifics at us and I think you''ll get more helpful replies. What''s your experience level, what size boat (in feet or $$) will you ultimately be cruising, and what do YOU mean by ''cruising''?