Just chatted this weekend with one of my buddies that will be helping me. He is a very experience boat guy, and done a lot of this kind of maintenance on many boats, small and large, just not my specific one. He understands the process and how to precision fit and align the coupling, so I feel comfortable there. So, between him and my other buddy who is a qualified machinist type person, I feel we can tackle this.
I am going to try and get the broken set screw out before I haul the boat and make sure I can get all of the bolts loose and get some PB blaster in there well before.
I feel like I have a decent chance of getting the old coupler off since I KNOW that it has previously been removed within the last 10-12 years to get the PSS seal on it. I'm going to purchase a new coupler anyway, so if the old one is unusable, or it won't come off and needs to be cut off, I have a solution to reassemble it using my existing shaft.
I plan on sliding the shaft all the way out, cutting the old cutlass bearing out carefully, and installing a new one using the washer/bolt method, then work on reassembling the shaft, PSS, and coupler.
My timeline will be as follows:
Friday afternoon - haul & pressure wash. scrape hull and tape water line, check for blisters.
Saturday morning - Paint & shaft removal simultaneously with three guys
Remainder of Saturday - shaft and seal work, more paint
Sunday - check and make sure shaft and seal is perfect, anything else that needs to done to the shaft/hull, document any blisters for next time, document dimensions of shaft so a new one can be pre-ordered in the future.
Monday - back in the water.