It's a Challenge
I have launched and retrieved my H23.5 single handed many times and it presents some challenges. You need a good ramp that's well protected (no waves) and is not very busy. That usually limits things to weekdays. My best success has been to float the boat off the trailer to a dock nearby and secure it while tending to the tow vehicle/trailer. Most ramps do have a dock handy so it's not a problem. I've reversed the procedure for retrieving and find that this works better than trying to 'motor' onto the trailer. It's easier to control things by pulling on a rope and the keelboard, motor and rudder are already up. This would be a nightmare if there's a line waiting for the ramp because it takes me nearly a half hour to retrieve alone. Draining the ballast, repositioning the boat on the trailer, etc..... singlehanded is slow. Any crosswind causes problems too. Procedures like this do improve with practice, however! The key here is a well protected launch ramp. If your kids are school age, they can be a big help here. Put a PFD on them and put them to work.These boats aren't set up too well to sail single-hand. Not as handy as the Catalina 22 but..... once I bought an autopilot, it got a whole lot simpler.The problem is the winches and rope clutches on the cabin top are almost impossible to reach while holding the tiller. Put one of those kids on the tiller. Your kids will grow into being real helpers and when they get really good, they will abandon you.KenS/V Wouff Hong