interesting you should ask
Last season myself and my two brothers bought a 1985 Hunter 28.5 which we are generally happy with.The surveyor said we would get one more season out of our tired cutlass bearing and then it must be replaced. So, as intrepid do-it-yourselfers we set out to replace it a few weeks ago. I bought a prop puller to remove the prop (you know what they say...the right tool for the job and all). Only thing was, nobody told the prop that it was supposed to come off when attached to a puller. However, somebody did tell the bronze prop shaft that if the prop doesn't want to come off, it's ok to bend instead. So, now we had a bent shaft, a stuck propeller, and were no closer to our cutlass bearing goal. So since the prop wouldn't let go of the shaft, we set about removing the shaft from the boat. This required removing the drive flange that the shaft is pressed into, and bolted to the Yanmar's transmission. Yep, that old rusted flange was all comfy and refused to budge. Not for hammer blows, not for liquid wrench drenchings, not with modest heat (I don't own an oxy torch, so I tried mapp gas for yuks.) So, we ever-so carefully cut the flange off, avoiding any further damage to the prop shaft. However, we could not get the shaft off the boat without removing either A) the rudder, or, B)the cutlass bearing strut. After flipping a coin we opted for the strut.At first, the strut did not want to come off the boat, but we were patient and managed to coax it off after 30 minutes of prying on it, and ever so gently putting some leverage stress on it from the prop shaft. Success. The strut came off, the shaft came out, and the prop...well it refuse to budge.So now the shaft, the cutlass strut w/worn out bearing, the cut-up flange and the stubbornly attached propeller are all nicely tagged in the marina office waiting to be picked up for re-work, or replacement or a little of both, whatever is best.There are two ways to remove the cutlass bearing. With the shaft and the strut still on the boat, but with the propeller off, a special tool can be used to slide onto the shaft so it's used as a guide to hammer the old bearing out. With the strut off the boat, the bearing has to be pressed out. I think you are wise to farm the job out to a pro. We, on the other hand, wanted that warm DIY feeling, and we are paying the price. Mike