ASA and PSIA Instructor
Join Date: Apr 2000
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You have selected a nice set of boats, all are personal favorites of mine. If trailering were not an issue, I'd go with the C&C 25, a sweet boat. However, while you can load one of those on a trailer, I don't beleive its really something you can launch from a trailer, I could be wrong but I don't think so. If you want a boat you can launch/retrieve on a trailer, I think you need to go with the S2, which IMHO donesn't involve any bad tradeoffs. I expect based on the ones I've sailed, its keel is a daggerboard, not a swing...you might check with S2 owners as to whether there are any issues but I've never heard anything bad about S2s.
Also, I continue to believe your comment about the C&C wet decks is completely an urban myth - I've never heard a C&C owner complain about wet decks, a friend of mine has owned a 33 for 25 years and its looks like new and he's never repaired or replaced anything other than maintenance of engine, ports and sails. I expect C&C decks are not more/no less prone to developing wet spots than other makes of similar age.