Although I have only owned 2 sailboats (a Seafarer 26, and 30) I am pretty familiar with them - have redone alot on my current 30'er.
I have seen pics of the 26, and it is basiclaly the same design as both of mine.
I believe your cutless is mounted in a prop strut. And, as you mentioned, when you try to pull the shaft aft, it will hit on the skeg (ahead of the rudder). I think you will find that is is mis-aligned a bit on purpose, and if you put a large pipe wrench on the strut, with a long pipe on the wrench for powert, you can temporarily twisting it enough to have another person pull the shaft clear. I was a bit leary of damaging the bronze strut, but an experienced diy'er told me it was common to do that. My prop shaft passed by the skeg on the port side!
If you don't want to try twisting it, you can afirly easily loosen off the engine mounts, raise the engine enough to have the shaft pass out underneath it. I would be very careful to mark (perahps with paint, etc) the position of the upper and lower nuts on the engine mounts, so you don't need to re-align the engine afterwards.
If you take the shaft to a machine shop, they may be able to repair the end.
here's a link to some of the pics form my work on my 1978 Seafarer 30:
Dscn0810 - Cleaned / painted engine compartment and engine Cruisers & Sailing Photo Gallery