At the shorter end of your range (22'), there is the Marshall 22 catboat (Marshall 22
). These are available in cat and sloop rigs (as in the photo here). They typically have an inboard diesel and have been in production since the mid-60's.
They are beamy (10'2")and arerelatively heavy for a 22 footer (5660# displacement vs. 2200# for a Catalina 22--which has a beam of 7'8"). The centerboard retracts completely and the propeller is protected by the keel/skeg.
They are not cheap, but hold their value better than most used boats. They will point better than most folks think, are very good in light air, and can be single-handed. You won't have standing headroom in the cabin, but you will have a generous cockpit and the boat will stay on her feet when beating.
I had an 18' Herreshoff catboat for 16 years, before moving up to my 35 sloop, but would consider the M-22 if I downsize in the future. The catboat started out as a workboat over a hundred years ago and is very user-friendly in most regards, as long as you reef (the cat rig in particular) when you first think about it.