I've done it a few times
I almost always raise and lower the mast on my C22 by myself. I agree that the worst problem is that the stays tend to get caught on various fixtures (usually the winches on my boat). One tip I have seen but not yet tried is to use masking tape to organize the stays prior to raising the mast (the idea is that the tape will tear when as the mast goes up). I have also heard of folks using the mainsheet block & tackle to extend the jib halyard so that they can essentiALLY pull the mast up, but this seems to me like it would put a lot of stress on the maststep.The other OBVIOUS problem is keeping the mast up. I just tie off one end of the jib halyard to a bow cleat and pulpit, then when the mast is vertical, tighten the halyard and tie the other end to a cleat on the mast.Also, make sure your hatchboards are in and that you stand as far back on the sliding hatch as possible.I find getting the mast up easier than on my old boat, a Potter 19 due to better leverage. Of course a mast raising system would be better, but I wonder if it is overkill and a waste of time.Dave BoltonDenver, COdavebolton@yahoo.com