I would not try to raise or lower my 23 mast myself - it is just too hard to keep centered as it is raised (or lowered), even though I fashioned something like baby stays, which do help, and the PO had added a gin pole. I remove the jib from the (Harken) furler, which makes it easier as you are not wrestling with the weight and bulk of the rolled sail. The biggest challenge is pinning the mast foot. The 23 mast is rather tall, and when it is positioned ready to be pinned more of its weight is aft of the mast crutch (at least on mine). So it wants to tilt back, lifting the foot. The pressure needed to keep it down while you pin it is not all that great, but it is very awkward nonetheless.
Using various attachments like the baby stays, and a line to help hold the foot down as I slide the mast aftward (when raising) I can minimize the time I need from helpers, but I still feel I need some extra help. I built a wooden extension that bolts to the top of the crutch, that raises the level of the mast about 2 feet, and has a rubber trailer roller on top. That also helps, but there is one point where the mast has to be lifted a bit to get the spreaders past (further aft of) the crutch, which is a lot easier with at least 2 people. If I could get that crutch about a foot further back, it'd be easier - but the transom position and angle, given the use of the pintles to support the crutch, makes that all but impossible.