Zach, this has been a frequent topic on these boards, so here are my 2 cents from personal experience.
I recently bought my first sailboat, a 35 footer, with which I''m learning to sail. My sailing experience is mostly limited to crew on a Schock 35 and Catalina Capri 26 for a summer of beer can races. The Catalina taught me only that I didn''t want a small, very slow boat.
I bought the larger boat for speed and comfort. I have a large family (3 daughters, wife, nephews, neices...), many friends and business relations in San Diego, so 33'' seemed like a minimun LOA for me. There are more modern, smaller boats with huge beams that are roomier, but they were out of my price range, or not well recommended.
The first shock of the larger boat was the much larger loads on sails and rigging
, and much more powerful forward inertia. Much more care must be taken around loaded winches
, sheets, etc... The second shock was the first time the boat got a little out of control in a freshening breeze. Beating across San Diego bay in 20 knots true, with a rail in the water, limited room to manuever, no experienced crew, while trying to remember all those tips on how to blade out the main and genoa, was like taking horseback riding lessons at the Rodeo!!
ON A LARGER BOAT, IF YOU HAVE LIMITED EXPERIENCE, YOU MUST HAVE AT LEAST ONE EXPERIENCED CREW!
Oh yeah, the point. If I had to start again, I''d have taken lessons at a sailing school on a J22, C22 or something like that. If you''re young enough and don''t mind getting wet, do some dinghy
sailing. I would also immediately join a one design sailing/yacht club, even if I didn''t have a boat. Lots of sailors talking and doing lots of sailing.