Like all the rest of the wannabie's liveaboard bluewater cruisers I have been researching this now for two years. It boils down to person tastes and where/what you are going to use the boat for and how handy a sailor is at fixing things. Just for arguement sake here is my list.
Hull - Fiberglass, modified fin keel
Deck - Fiberglass, no teak ( leak waiting to happen, more maintance, and cannot walk on it in the tropics to hot)
Size -38-42 feet
Tankage - min 100 gal fuel, 150 water
Storage - Can never have enough
Heads - 1 real nice one vs 2 small ones
Saiplan - vote is still out Sloop, cutter or ketch
Cockpit - I prefer aft, the CC that I have seen from older boats 1980's I don't like, to small and in my opinion dangerous. I haven't seen enough CC in the newer designs to rule them out. I do like the CC layout in the salon area though.
Just my thoughts so far