number of possibilities
There are a number of boats in that size range and trailerable that may meet your requirements. This is just a short list of the ones that came within my radar when I was looking earlier this year. My requirements were under under $5k, under 2000#, under 20', swing keel or shallow draft, sitting headroom cabin, self draining cockpit, cockpit lockers, and anchor locker.My research found several boats that met most of these criteria. Most are out of production, but I was looking for a used boat anyhow. My findings were:Sirius 21, Halman 20, DS20, O'day 20, Precision 21, West Wight Potter 19, Seaward Fox 19, Venture 21, Compac 19, Cal 20, Mariner 2+2, Sandpiper 565, Edel 540 and Siren 17. I ended up finding a Sundance Weekender 20, that met all my needs except an anchor locker, which I can retrofit under the forward hatch.Some boats were more popular in some parts of the country than others. I found mine within a mile of my yacht club. I was lucky!