At your price point start thinking Alberg. Most of the other boats you mention are well above that. A late model pearson such as a 303 or a 28-2 will give you both the private head and head room you are looking for.Are you going to buy on the west coast? If so that is going to effect your buying power per boat buck and limit your choices.
I would narrow it down to four boats and then search to see what is available. If you are both on board with the dream, go for it! lots of luck.