It does take some time
Ken: It takes us around 3 or 4 hours to set ours up, and we've been doing it for years. But this is setting it up for a season. Also, when we trailer our boat, we only have the cushions, sails, life jackets, and fenders in it. If you carry anything else, it could wear a hole into the fiberglass if it is trailered too far. So, this amount of time includes putting everything where it belongs and hooking up the battery, filling the head with water, putting the motor onto the motor block, putting the main sail onto the mast and boom, etc. It doesn't include adjusting the rigging. Putting the mast up isn't a big deal, but you do have to reconnect the forestay, and the 2 forward lower shrouds. Also, one of the upper shrouds should be loosened before raising the mast, or you could overstress something. I always loosen my port one 10 turns before taking the mast down, then retighten it 10 turns when I raise the mast. All this does take time, and doing it after a day on the water really wouldn't be a ton of fun. I don't think that you will use your boat much if you trailer it every time you use it. If you do put it in and out every time, be absolutely sure to install a guide onto the trailer, so that the keel will center itself into the rubber "V" on the trailer.We kept our boat on the trailer at a marina for 2 summers when my boys were little. It was a little rough on the boat, putting it in and taking it out every time. But it was on the Susquehanna River, and there was current, which was certainly part of the problem. You might want to call Maryland Marina, which is near Essex, MD. That's where we put our boat into the water, (but not where we keep it). They have several options that could work for you including keeping your boat on the trailer, or I have seen them put C-22s into the water with a big forklift. Do you sail from Middle River now?Aldo