When single handing, I use a gin pole (winch mounted on gin pole), and baby stays. I found the baby stays are essential for stabilizing the mast horizontally. Because my shrouds are aft swept, they take over as the mast gets more than half way up for any side-side sway.
I mounted strap eyes to the mast (about 6ft up on a 25ft mast), and tied some nylon 1/4" line to the eyes. The baby stays run to deck mounted blocks that are 2" forward and 2" lower than the mast tabernacle pivot pin, then run to my jib sheet jam cleats. This makes the baby stays tightest at about the 45 deg point of mast raising, which is when sway is most dangerous for my mast and tabernacle. And has the added benefit of stopping the mast pivot pin from backing out the back of the tabernacle. The baby stays are rigged before raising the mast, and removed after the mast is up.
When there are 2 to raise the mast, I save time by walking the mast up myself, and have the helper tend the jib halyard. My mast is light enough to stabilize by hand as I walk it up. Rigging and unrigging the gin pole and baby stays adds about 30 minutes to the mast raising/lowering process but is the only way I could come up with to do it safely single handed.
I engineered my system myself, learning the hard way (dropping the mast). My first gin pole broke where it connected to the mast. And my 2nd gin pole was a disaster in some crosswind without baby stays.
Fred W
Stuart (ODay) Mariner 19 Sweet P