Cool, I just went through this exercise... Here were my criteria for buying a boat. (not in order.)

1. Designed to handle well both 1-up (main alone) and 2-up (main and jib.) (I define this criteria by the speed of the boat being comparable in either configuration. i.e., the Texel ratings are about the same.) I sail alone about half the time and especially when racing, but when my wife is on board, she wants to be a crew member, not a passenger.
2. Has asym-spinniker. I just like the way they look.
3. Light weight, easy to handle on land, possible for one person to rig/derig. I do most of the work on my own.
4. Optimized for a 1-up crew of about 70kg, 2-up crew of about 120kg. We are pretty small people by Western standards.
5. Faster than a Hobie 16. If I want to go slower, I can just use the boats at my local sailing center.
6. Trailerable without breaking down the entire platform. It's bad enough having to take the mast down.
7. Cost less than $10K US including trailer and beach wheels or used boats in that price range are available. I'm not made of money.

What boats fit the above?