I also posted our progress in another thread. We're in the Great Lakes and are doing this before we put the boat in the water for the season. The rudder has enough room when in it's cradle to drop the rudder.
The rudder wasn't too bad once I folded my legs into positions not described or achieved by even the most accomplished yogi and squeeze myself into the rear locker. That was relatively easy.
The prop was a nightmare. The nuts came off fine, but I wasn't using the right tools. I was using a C-clamp with a split end, but it didn't have a place for a ratchet handle, so I couldn't get enough force. After 4 hours of trying all manner of things, I finally went and rented a prop puller from a local yard. It came off in about 30 seconds.
The prop shaft was really stuck in the coupler. We ended up attaching a piece of metal and banging on it with a hammer. It bent the end, but the prop shaft was toast anyway. That took a few hours.
The cutlass was long, slow, and tedious, and we stumbled on some oddities, but it did come out after cutting some wedges with a hack saw blade, and then putting a socket wrench socket with an extension down the tube and banging on it with a hammer for a bit. Our stern tube is made out of ceramic or something. I was expecting brass. As such, I had to be very careful when prying, as I'd damage the stern tube.
Now I'm trying to order all the parts. I'll be replacing the cutlass, which started this whole thing, the prop shaft, possibly the coupler, depending on what the shaft company thinks of it, at least the rubber tube that holds the packing nut, and maybe the whole packing assembly.
I guess I have never seen a dry bilge to appreciate it, but I just planned on continuing to use the regular old packing instead of the pricier PSS. We've been able to do all of this ourselves with some help from other sailors, so our total out of pocket cost will be:
New prop shaft: $200
New cutlass: $50
Prop puller rental: $25 (Nice guy)
Short length of rubber tube: $15?
New packing: $25?
TOTAL: $315
It was frustrating, but we learned a lot about the boat, and got to take a peak at things we should be doing each season for maintenance (checking the packing to make sure this shaft doesn't get damaged).