Do I have all your answers! During the pre-purchase survey, I was told the cutless bearing was worn, so at the fall haul out, I was able to remove my shaft past the rudder with a lot of strain on the strut and old cutless bearing. Had to grind 2 slots in the front flange to remove it. Bought a new split flange, replaced the packing in the stuffing box, replaced the hose to the shaft log. There was a lot of wear at the rear of the shaft, and a little at the front. Got a new SS shaft from Proper Pitch in Selbyville, DE. Was able to hacksaw and twist the old bearing out of the strut, after removing the 2 set screws, then hone the hole smooth. After searching all winter for a shop/tech to install a cutless bearing, I found Ken at WeekendRProducts who shipped to me a Bearing Buddy tool to rent, and a new bearing. He is very good to work with. To do this again, I would get all the parts ahead, grind the front flange off, rent the tool, press out the old bearing, remove the old shaft, hone the strut hole, then install the new shaft, press the new bearing in, then install the front flange, stuffing box and hose, then the prop. No need to drop the rudder, lift the engine, unbolt the strut etc. Once the old cutless bearing is out, it is easy to remove/install the prop shaft past the rudder. (At least it was on my 1985 Hunter 34). With a new shaft and flange, you will want your machinist to "fit and face" the flange to the shaft, to make sure it is perpendicular to the shaft. Have him make the flange a hand pressure fit on the new shaft, no room to tap it on once in the boat. After the shaft is in, and the boat is in the water for awhile (having been on stands while you did the work), you will want to measure the clearance between both flanges, so that they turn true to each other. With feeler gauges, you should have no more than .003" difference in clearance between the flanges. If so, loosen and adjust engine mounts. Your price of 500.00 sounds right, I wish I had someone who could have guided me through this, hope all goes well, feel free to ask for assistance.
John