I lubed the heck out of everything!
Just my opinion, but...
As I said, dropping the rudder was not a huge deal, the hardest part was removing the shaft flange. You can tell me I'm wrong but if the cutless is shot then the hose that connects the stuffing box has not been replaced in the same amount of time (probably 25 Years). There is no sea-cock for this hose in case it leaks! Once you get to the back of the engine you can replace this hose, re-pack the stuffing box and since you had to remove the exhaust hose it is easy to remove the heat ex-changer and replace all the hoses back there, not a place you want to spend much time but once it is done you don't need to spend much time back there in the future.
PS: That hose I removed, which I belive to be the original from 1987 was not as thick walled and did not have as many plies as the one I replaced it with from Buck-Algonquin. I had to buy a foot of this hose, only needed 4 inches so I still have 8 inches left and don see that I will ever need it again.