Wow, the work on the shaft and stuff is way harder than I was expecting. I've known for a long time you need good tools, but in this case - you REALLY need the pro quality. I worked on trying to get the prop off for about 3 hours and finally called in the yard mechanic. We had the prop off in 10 minutes. Same with the coupler on the other end of the shaft. I tried for about 30 minutes, went and borrowed his tool (we kind hit it off over past experiences, he doesn't normally lend tools) and then had the coupler off in no time.
Working on the cutless bearing now, it was definitely worn out. I going to try and rig up a press with some all-thread and random parts. I may end up cutting it out. Wish me luck !