Re: The Search Is On
Tanzer 22 and San Juan 21 are both very common up here in the PNW.
Everyone that I know who has owned a SJ21 has loved it. I think it's probably ideal for your use. It is a lot smaller and lighter than the Tanzer, which should make trailering and re-rigging a lot easier.
The Tanzer 22 is well regarded too. At my old marina I was surrounded by them (there were 4) in a marina with about 14 slips), but I never had a chance to sail one. They are said to be fairly fast, though I always found the design to appear to try and cram a full cruiser into 22'.
Personally my bias would be towards the SJ21, but I'd pick whatever is the better boat (condition/quality) for the price.
I'm no longer participating on SailNet.