After I've gone out a few times in quick succession at the start of the season, I find that raising/lowering even a keel-stepped mast single handed is easy and totally the quickest method (being North of 6' definitely helps).
Key ingredient is having a
hinged guide above the hole. I would have thought that a tabernacle would serve the same purpose (fixed pivot).
While the keel-stepped mast is longer, it's secure the minute it's dropped on its step.
My own
mast-raising tripod, which I use when I don't feel like lifting anything, is designed to accommodate the short vertical raise to get the mast out of the hole, as well as the tipping. (Hence I cannot use an A frame on my boat).
My contraption has to be rigged and unrigged for each use, making the process slower. Otherwise it gives the same positive control except for mild swaying, when the mast is partially up. As a light steadying hand is all that's needed, I'm not planning on rigging any extra lines.