Boat choices
Jim: I went through the same process you are now undertaking. Because family responsibilities (the births of my children) delayed my actual purchase of a boat, I had about six years to research my options.I too wanted a boat in the 20-25 foot range, mostly because I was comfortable with my ability to handle that size boat, and the realization that I would be almost exclusively day sailing, with some possible overnighting. I did not know if my wife and kids would ever want to do more, and I did not want to tie up more time and money than necessary in the boat.We had timeshared in a Catalina 22 before, so I was very familiar with that boat. I have found them to be well made, and very robust. Catalina makes so many of them that they have been able to iron out production and design problems. If the boat has been well-maintained, you will find that you can't go wrong with a Catalina 22. You will almost always be able to sell it for what you bought it for, a rarity for small boats.However, I wound up buying an O'Day 23. My main reasons were: a head separated from the main cabin by a bulkhead and a door. My wife greatly preferred that our boat have this feature, and I agreed. It really does make a difference, whether day sailing or cruising. There really is no comparison to the Catalina's curtained off, under the V-berth arrangement. Second, I really preferred the O'Day's keel/centerboard arrangement to the swing keel of the Catalina. Despite its history, and the fact that I never had a problem, I was never wild about 500 lbs. of lead swinging around under the boat. Although I have had a problem with my centerboard sticking in its well (see my article on this website), the problem is easily handled. Like you, I find that the trade off of somewhat diminished windward performance with a centerboard is more than offset by the advantages of the lesser draft. Especially if like me, you plan to sail close to shore. We have been very happy with the O'Day so far.For what its worth, I also considered the Catalina 25. I never considered the swing keel version (an even heavier weight potentially flopping about), but I really liked the fin keel model. It is however a real step up in terms of weight and comfort. Of course this also translates into additional systems complexity, maintenance costs and problems, etc. Not worth it for me.So you wanted advice, you got it.Good luck.