Looking for guidance on model of sailboat to buy
This is my first post here, I apologize if this isn't the most appropriate category to post this under.
I'm looking to get a small day sailer and I'm overwhelmed by all the models out there. I sailed a bit when I was in my early teens on Blue Jays and Lasers and Sunfish. Then a few years ago I took a fairly intensive course in the SF Bay Area that licensed me to sail up to 48 ft boats.
I'm looking for something I could likely sail myself eventually, but that would have room for a couple other people or more. I'm thinking somewhere around 20-25 ft, but I'm open. I live in Portland, Oregon, so I'd likely sail in the Columbia as well as other nearby lakes if I end up with a boat I can easily trailer.
Ideally I'd only spend a couple thousand dollars, but again, this is a little flexible. I want to get something that I'll really enjoy.
Does that seem doable? Any suggestions on makes or models to look for, or top steer away from? What else should I look for when I'm checking out boats?
Thanks for any advice to this newbie sailboat buyer!