Re: Pearson 33-2 Wing Keel or Pearson 34 Centerboard
My sense is that there is a somewhat significant difference in pointing (at least in racing terms) but I haven't raced my boat (the fin keel) much, so it is hard for me to compare.
On the boat I race on (the centerboard) - we match up pretty well with a Hunter 35 (they have a faster rating, but we can beat them boat for boat sometimes) but it can be frustrating to start with them and watch them climb towards the mark faster... There is a Tartan 342 that we can beat on corrected time sometimes, and a Contessa 33 that is running away with it this year. Other boats are smaller (C&C 25, Morgan 27, and I forget what else) and behind us in the standings. I never know how much to attribute to crew and skipper vs boat performance though.
The skipper of the Hunter says we can't match him in tacking because the long keel/centerboard trunk slows down our tacks, but I don't know if that is true. With the long shallow keel you can actually sail to windward without the centerboard down.
I single hand my boat a lot, and it works fine, but the boat really isn't ideal for that. The winches are not accessible from behind the wheel, and the cabin top traveler is out of reach. It is not a great arrangement compared to a tiller steered boat with everything in reach of the helmsman- but, that said - I single-hand all the time and love it. The single best addition I have made was a Dutchman boom brake with the control line led to the helm - makes gybing, and sailing wing-and-wing easy.
Personally, I am not crazy about centerboards... the raising and lowering... it seems necessary, and yet you don't get the immediately noticeable feedback you do from improving sail trim (or maybe I am not observant enough). But I guess they are a great compromise to a lot of people, and I envy the shallow draft at times. I am kind of curious about wing keels, but I think if you ground them, they are harder to get free.
I would say the boat is family friendly... pretty stiff I think, and nice big interior. I usually reef quite early when solo or with non-sailors - I put a reef in the main around 12 knots, and roll the 135% genoa part way in around 15 knots or so... then she settles down up into the 20's. My main is kind of old -- I think with a new flatter main I could postpone reefing longer. I have sailed the boat in about 25-30 knots and 8 foot (or so) seas off the Jersey coast on the delivery, and she handled it well.
I'll try to help with whatever info I can, and see what else I can think of that might be relevant. For what it's worth, I bought my boat on the northern end of the Chesapeake, but I don't know your particular sailing area.
Western Long Island Sound