Greg Lepore gives good advice if you are going to sail in the same water. In my racing days we did exactly that. Boats were stored on trailers fully rigged.
If you want a trailerable day-sailer that you can take to different waters easily look into a MacGrgor 26. It fits all your criteria. Headroom, swing keel, trailerable on a low trailer, rigged in 15 minutes.
https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&cad=rja&uact=8&ved=2ahUKEwjHz9mVm7HkAhVyzlkKHTrLD-UQFjAAegQIABAB&url=https%3A%2F%2Fasa.com%2Fnews%2F2017%2F07%2F24% 2Fcruising-boat-spotlight-macgregor-26m%2F&usg=AOvVaw0bRCBc0YCG7Bgjco8hORc0