We regularly raise and lower the masts of 23 and 27ft Hunters. It generally needs about 4 people. could do it with less if you made an A frame jig and used a winch.
The smaller hunters with the OB lifting mechanisms were designed for 5hp 2 stroke short shaft engines. Under powered and as mentioned prone to leaving the water if you motorsail on the wrong tack. We use a 4 stroke 8HP long shaft so it is too heavy too big and too long to raise, so it stays down all the time. but the prop has never come out of the water.
