There is a BIG diference between a 22 footer and a 27 footer. The first is easy to trailor sail and fix on your driveway, the latter you are in to marinas and boatyards.
2 up a Catalina 22 Oday 22 or similar will give you lots of fun and can be overnighted in quite comfortably.
4 up you want something like a Catalina 27 try to find one with an inboard diesel. It will be easier to resell. This will feel more like a big boat and is likely to have a proper toilet with holding tank.