You've missed a couple of good boats to look at. I would suggest the best sailing boat in what you are looking for is a Holder 20. There are 2 versions, 1 with a short cabin, and the second with a longer cabin. It will be fast, but yet has a weighted drop keel, so should be reasonably stable.
The second consideration would be a RL 24. It is a little bigger and heavier at 1600 lbs. Nice size cabin, and yet light for its size. It is fast, but reasonably stable. I have sailed in 30 mph winds with full sails up and had a blast. It has a weighted swing keel.
Both of these boats will sail far better than anything you are considering so far. Both are fast, responsive boats and popular competitive racing boats. The RL is not well known in the USA but is much better known in Australia where it was designed.
As for weight, Anything in the 1500, 1600 lbs will probably exceed your 2000 lbs limit. The heavier the boat, the heavier the trailer. If you are cruising, you will also be tempted to fill the boat with junk that adds up pretty quick. Interestingly, my RL pulls much easier than my first boat, which was a American 17. The reason is that the American had a stub keel, which made it sit high on the trailer. (just like the Starwind you are looking at). The boat sat high in the wind, and was difficult to pull at speed. On the other hand, the RL sits low on the trailer, out of the wind, and pulls easily at HWY speeds - 80mph+