I don't think I'd want a pop-top O'Day in May or October in Chi-town.
I don't think I'd want to live on a 23 footer if it wasn't a Georgian 23.
Could happen in your price range.
If you're trailering that much already you could maybe find a Grampian 26 with a swing keel (they made a few), same designer, and a lot of boat for 26'.
Zed has hit the mark. Georgian 23, bayfield 25, Challenger 24, Grampian 26 all have full headroom, enclosed heads, shoal draft for ease of trailering, hanging lockers, and all are sub $5K for a solid, if basic, boat.
We bought our Georgian 23 six season ago with the intention of sailing her for a season, to see if we enjoyed sailing, then getting something slightly bigger.
We are still sailing her, simply because we can't find a boat with a diesel inboard, dodger, bimini, furling jib, autopilot, masthead rig, shoal draft, full headroom, etc., 26 feet or under, without starting to spend serious cash.