Little chance of being disappointed
If you will be only occasionally overnighting and want to really trailer the boat (keep it in your driveway and launch it every time you use it), then there are a couple of obvious choices: the Catalina 22 and the Oday 22. I wouldn't go with the Oday 23 (much heavier and more difficult to pull) or the Catalina 25 (even heavier). The biggest differences between the Oday and Catalina: the Oday is a swing centerboard, meaning the ballast is contained within a stub keel and the centerboard is relatively light and easy to raise or lower. On the Catalina, the ballast is a swing keel, which means the centerboard itself contains the ballast and requires a crank system to raise and lower. I prefer the Oday system. Note that some old models of the Oday 22 did not have a centerboard, only the stub keel. I would avoid these as they do not sail as well as the centerboard models.On the Oday, the "head" is separated from the cabin by a bulkhead with a door; on the Catalina, the portapotti is under the v-berth and practically in the main cabin. You can rig a privacy curtain, but if there is one thing I have learned that is important to women on board, its head privacy. Just you and your son? Maybe not an issue at all.The Catalina 22 was available as a pop-top. This provides standing headroom in the main cabin. A big plus. I don't think the Oday 22 was ever offered with this option.One other difference is that Catalina is still in business and they still support all of the old boats. I don't think this is a huge advantage, but some like the fact that OEM parts are available. Also, the Catalina 22 is the most popular production sailboat ever and tends to hold its value.You can probably find either boat with a trailer for around than $5000. Either way, you will have a great boat and won't be disappointed.