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Westsail 32 Cutter
Jeff always does a nice, thoughtful job answer queries like yours, as you can see. I''d throw in a couple of add''l thoughts...
1. Think displacement vs. length, both in choosing a boat & and also when considering price. It''s just one measure of what you should be looking for (and getting for your $) but it''s a useful exercise. E.g., I''m cruising a 42'' Ketch in the Caribbean right now (well, when I''m there...) and it happens to be about the same displacement as the Westsail 32. Do you need my 42 footer? By asking yourself ''Do I need 21,000# of boat, all loaded up?'' you''re doing about the same. OTOH after 2 rainy days during a vacation cruise, when the kids are climbing the bulkeads, you might say "YES!"
2. Ask yourself whether you are purchasing a boat to ''sail'' OR purchasing a boat with which to begin climbing the ladder that leads to becoming a cruising sailor or ''seaman''. To the extent that time constraints, the demands of a family, building a career, improving the house, etc. are your priorities, then buying ''older but bigger'' is just not the choice you mean to make. (In my definition, a W32 if both ''older'' and ''bigger'').
3. It''s hard to believe it as you wander around boatyards (IMO "the" best place to begin boat shopping, not the broker''s office) that there are creampuffs out there among the older boats, but there are. They are often behind folks'' homes in waterfront communities, tenderly cared for by owners that finally grow old and need to move down, to a power boat, or out of boating altogether. (Why are they old? We were talking about waterfront communities, right...?) These are the boats you''re looking for. They''re also the ones everyone else wants...so as in all other endeavors, you have to work a little harder and be a little more innovative to find what you''re after. That means networking with work/church/community friends who know someone who... and things like that. Brokers might have a few, too - but they talk to a lot of people, so the creampuffs are harder to find thru them.
How about a Tartan 34 (just a tad more than 50% of the W32, displacement-wise)? Or an Endeavour 32 (the centerboard model)? These kinds of boats, despite being built somewhat inexpensively, came before the iron ballast and all-liner interiors of a Catalina or Hunter and, if kept up, are worthy of consideration.