Greig-

I replaced the cutless several times on my C30. After removing the prop shaft, I used an unorthodox approach, but it always worked. The cutlless bearings are made from a soft sleeve of brass with vulcanized rubber on the ID. The brass sleeve is deformable. I would carefully insert a thin bladed screw driver between the brass sleeve and the strut bore - with careful tapping on the driver handle with a hammer. Angle the blade so that it bends/creases the brass sleeve into the bore of the strut. Sturdy needle nose pliers and vice grips also come in handy in expanding the crease along the length of the sleeve. The crease allows you to collapse the bearing. I also use a large diameter bolt and hammer to tap the sleeve out of the strut housing. If not careful, you can score the inside of the strut housing. If you do that, you'll have to carefully sand down the high points where its been scored (wrap sand paper around a dowel or bolt) or it will interfere with the insertion of the new bearing. Do all this with patience and you should have minimal scoring. Double check that the C36 does not use a set screw to help retain the cutless bearing.

After cleaning the strut up, you can insert the new cutless bearing by hand and SLIGHT tapping with a block of wood between the bearing and hammer. The bearing will easily deform so be sure to tap it squarely and check that it is inserting straight. You will probably only get a 1/4 inch of insertion or so before you meet a lot of resistance. At this point, you can use a home made screw press.

Buy a 3/8 or larger piece of threaded rod from the hardware store, and some nuts and large washers. Cut the rod so its several inches longer than the strut length. Drill a 3/8 hole in two blocks of wood. Hold one block of against the strut and the other against the bearing end. Insert the rod through the assembly and attached the nuts with washers. Slowly apply torque to the nuts. Make sure that the rod is centered in the strut, or the bearing will insert at an angle and be damaged. A little lubricant may help. Don't force insertion. When you get to a point where the bearing seems hung up, tap on the threaded rod with a hammer and then reapply torque. If you get to a point where the bearing won't insert without deformation, carefully cut it adjacent the sleeve, debur the brass sleeve with sandpaper and insert it from the other side of the strut. There are probably readers cringing at my technique, but it works. If you have to cut the cutless in two, make sure that the water cooling slots in the rubber core line up before you start pressing the 2nd half into the strut.

I've read if to heat the strut with a small torch and ice the cutless bearing it will make the insertion easier. Theoretically, this makes sense, but a warm strut transfers heat to the brass pretty fast and I've never seen this work in practice.
Good luck

Greig, I contacted the person responsible for the C36 Assoc. toolkit and yes, Canadians are out of luck and they won't ship anything to Canada. At the recent Vancouver boat show I spoke with Osbourne Propellors and they said that they have a cutlass bearing puller for rent. It sounds like the Strut Pro model that the association has. I'm going to replace my cutlass bearing in a month or so and will try the tool Osbourne has. I was going to do a haul out at Granville Island boat yard in a month or two. Maybe we could do it at the same time?