I have actually raised and lowered mine alone, but ONLY out of dire necessity. The mast is heavy, and I think it is about 33 ft, so it will be like 40 ft above ground when on the trailer - make sure you avoid trees, utility lines. low flying jets, etc. I much prefer at least one helper, ideally two. When you slide it back from the stored position to pin the mast foot, more than 50% of the weight moves aft of the crutch, so it wants to tilt back and you have to hold the foot down while pinning - that is hard with one person. The only way I was able to do that alone was to use a line tied across the deck that held the foot about 6-10 inches off the deck as I slid it back. On mine, you also have to lift the mast up a few inches so the spreaders can go over the crutch a sit slides back, and that is very hard alone.
If you use a gin pole and also if you have a well-functioning baby stay system it is a lot easier. I have damaged my mast extrusion (minor rivet damage that was easily repaired) twice because it wants to sway side to side, pulling it off the pinned mast foot. Having 2 helpers is very valuable, as these 2 can support it sideways as it goes up or down. If you use a 4-1 block and tackle (such as the main sheet system) and your jib winch, the force to raise it is not bad - it's the sideways sway that'll kill you. The guy I bought from rigged a special block/tackle with a long line, as the mainsheet may be too short to let you use the jib winch. Watch the shrouds carefully as you raise, including the backstay - mine always seems to hang somewhere and I have to lower and then raise again. If you feel resistance on the winch, stop and look, don't force. Tape the ball fittings for the sidestays so they stay vertical while you raise or they tend to swivel and get stuck.
The previous owner built a gin pole from pretty stout walled aluminum tube, though I think something like electrical conduit would have worked - the weight of the mast going up is mostly along the lifting line and the jib halyard (if you use a gin pole) so the pole only needs to tolerate the force of the lines pushing it into the mast. Since the 23 lacks any gin pole, you have to fashion a way to fix it to the mast base. The triangular system recommended by Kermit's post may be the best. On mine, the guy used a pretty thick aluminum plate (I'd say 1/8) and bent it into a squared off U shape to straddle the mast extrusion, then drilled holes sideways through it and the mast to bolt it in place. The gin pole goes between the "legs" of the U and is held with one bolt so it can swivel. The tensioning of the jib halyard to the eye on its upper end and the lifting tackle on the lower side keep it in the right vertical orientation (just so it is above the deck when fully raised). The disadvantage is having to fashion that U bracket and drilling through the mast. I would not attempt to make a hole in the front of the mast to let the pole go inside, like the larger trailerable Hunters came with.