My short test mast is used to hold up small mills, and in the past with light ECMs etc, it hasn't been a problem to hook a rope to the mast and raise it will standing on the roof of the shed.
This changed when I beefed up the mast to 2" schedule 40 steel , and mounted a treadmill motor. Top of the mast weight is ~ 50 lbs. Took me 4 or 5 attempts to pivot it back up , and some pain pills later.
Thi time, I used garage door springs to take some of the load, and it worked. Reduced the perceived weight by half and had no trouble pulling it back up. I used 2 springs inline, but probably would have been better with one.
I did run a safety cable through te springs.
Photo with it down.
..and back up