Re: Charleston, SC - Help, please
It sounds like you will need to launch and retrieve your boat every time you go sailing. If it takes an hour (or more!) to step the mast, set the rigging, and get the boat in the water, and another hour (or more!) to get the boat on the trailer, lower the mast, pack everything away, etc., I can't imagine you having much fun - or the grandkids either. I'd give careful consideration to something that is easily rigged - like a Com Pac Eclipse or, if your budget can stand it, a Norseboat 21.5 Cabin version. Both are light enough (2000 - 2200 lbs) to tow behind a mid-sized SUV.
Then again, the price difference between a nice used Catalina 25 and the Norseboat is enough to keep a slip in a marina somewhere for years and years!