Our cutlass bearing was pretty warn (the boat was new to me), when I had it hauled a few years ago.
It mounts in a small fairing and is held in place with side mounted allen screws. They did not have to pull the shaft to remove the old one (although that is how it got all chewed up on the outside), they just grabbed it and pulled it out with a puller. The new one fits nice and snug and went on over the outer end of the shaft (with prop removed). I had my Maxprop regreased and reset at that time since it was already off. The replacement of the cutlass bearing was not expensive and is in line with what others have indicated.