[Edit: Serves me right to reply before catching up with all the postings. Walking away seems like the right call.]I would not characterize the 23 as a trailer sailor. The mast is heavy enough that I would only want to use it when you can keep it in the water, or at least only have to step/unstep a limited number of times per season. Also it is a rather tall mast, so when you slide it back along the deck to fix the pin into the Tabernacle, more of its weight is aft of the crutch before it is positioned over the Tabernacle. You have to hold the base down against this leverage in order to pin it - I consider that at least a 2 person job.
Fully agree. Once per season is doable, with 2 people: one to walk the mast up from the cockpit area (I built a ramp of 2-by-I-can't remember's [probably a pair of 2x10's] to walk on, and the 2nd person holding on to a halyard on the ground forward of the boat to help with the weight. Also, there is no "the crutch" as far as I recall. I think it's all whatever the owner built and installed themselves. As I said above, it was a puckering experience. There are plans out there for a decent mast raising system, which would be well worth looking into. It would be a very reasonable thing for 2 healthy guys if you had a rig to keep the mast from going off to one side. But IMHO, you need to keep this boat in a slip, or you'll end up not using it very much.