I have owned 16 sailboats in the last 35 years. These ranged from an ancient 30 foot sailboat with a wooden mast to high-performance racing skiffs to a handbuilt dinghy to my current 45 foot performance cruiser. Each served it's purpose in it's time...and I frankly fell in love with 10 of them, so my number 1 criteria for a boat YOU MUST LIKE HER!
My second criteria has always been PRICE. When I could only afford a beat up old Crysler dinghy (it was free)...guess what I had.
Third criteria is what you want to do with the boat. Do you want a fast boat, do you want to gunkhole up into creeks on the Chesapeake or cross oceans?
For example, as a young athletic guy, I had Flying Dutchman (at the time the fastest dinghy in the world) that needed huge amounts of work just to keep her from flipping over. But she could scream across wave tops like a banshee.
Later, I had a 22 foot South Coast with a swing keel. She was not fast or terribly comfortable, but she had two bunks, was cheap to operate and I could pull her right up to the beach or into any conceivably navigable bit of water. I probably saw more of the upper Chesapeake in her than any other boat.
A few years ago, I wanted a boat that was big enough to take friends or family out for a few hours but was easy to launch and fast. I picked up my second Hobie 16, which I sailed all over the Potomac (occasionally buzzing PSC boats). When I got the itch to start doing longer cruises with my family I decided to move to something bigger...