Thanks for all of the suggestions and advice guys.
The Westsails always get a bad rep, but I'd bet there's more people out there crossing oceans with them than making forum posts complaining about their performance! I didn't know their SA/D ratio was 15, that doesn't seem bad compared to other "cruisers".
I like the S&S 34, but the interior does seem small (and I'm not a huge of their layout/feel). Even though the PSC31 is tiny, it seems to have a nice feel to it. We'll be living on the hook or a swing mooring most of the time, but we're very minimal and don't need a big boat.
The Kendall 32 we're looking at is basically a Westsail with a flush deck. Nice to work on deck, and there's a bit more room below for books, etc. There's no wooden boomkin to worry about, just chainplates for the backstay. It also doesn't have teak decks to worry about (except on the bow/cockpit, but they're not screwed in to ply core). The only downside to this boat is it's engine, a Universal 5432 (Kubota core). It's very well maintained, recently mostly overhauled, but still getting old. The Westsail we're looking at has a 2008 Yanmar and all mechanical (gearbox, etc etc) replaced at the same time.
I'm glad there's forums like Sailnet to have these little discussions. I'm sure my wife is sick of boat-talk. I just want to make a wise decision, and choose a vessel that will suit our needs for a long time.
I forgot to mention that ALL of our sailing experience is from extensive time on a 15' racing dinghy, so things are about to get interesting
I learned so much from that boat and had so many fun adventures, sad to see her go.