When I did the dripless seal on my 27, I used a separate plate with drilled holes, bolts and sockets to drive the shaft out of the coupling. I did not use the flange on the engine. Tighten, kroil penetrating oil (protecting the engine shaft seal from it) tap, rotate, repeat. Took 2 days! Along with the new seal I replaced the cutlass bearing. Shaft and prop came out as one and went off to a prop guy.
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