I dont see why you would, you need to remove the prop . My prop would not come off. I had to remove my stuffing box and the inside transmission flange and I pulled the whole prop and shaft out together then I was able to slide my old cutlass bearing off the other way. If my prop would have come off like its supposed to this would have been extremely easy.
Oh yeah, you are probally going to have to take your cutlass to a machine/prop shop to have the old one removed and a new one pressed in..........and while your at it you might as well have them check out your prop(make sure pitch is right), and make sure your shaft is true.