I have seen the cutless bearings removed by just removing the prop and the shaft zinc, which is normally just ahead of the strut, and pressing it out using a tool for the purpose. Basically it was just a piece of pipe with ID to fit the shaft, and OD to fit inside the strut, that was sawn in half lengthwise to fit around the shaft. With the halves held by a hose clamp, a puller is used to pull the split pipe through the strut, pushing the old cutless bearing out ahead of it.
I have looked online for this setup, and cannot find anything, so I don't know if these are a custom tool, or if I just don't have the correct sources. At any rate, I have to replace the cutless and strut together, and I have them already assembled by John.
If you figure in having to realign the engines to the shafts, I'd say there is not a lot to be saved there.
1975 32' Flybridge Sedan, twin Perkins 6-354 diesels, 1:1.53 velvetdrives, 16 X 19 props. Merritt Island, Florida