Slowly sinking in Fort Lauderdale.
Drip drip drip, and drip again. That’s the water getting into my bilge at the rate of half a gallon per hour. It’s coming in through the drive shaft. The packing gland, it’s a fancy name for a very crude sealing system, has to be repacked. I’ve never done anything like that, who has? The nice part is that water is going to rush in while I’m going to take the packing out. Well, that’s only if I ever get the locking nut to move. The part I need to disassemble is one green block of oxidized metal. Up to now, all my efforts were vain.
I wanted to get this done since there was a window of OK weather to cross to the Bahamas on Monday. I didn’t know if it’s better to sink here or in the Bahamas but they seemed to have more boat yards in Fort Lauderdale. Since I’m living on the boat the leak is not that much of a concern. The bilge pump takes the water out every few hours and as long as I have battery power and a working pump I should stay afloat.
miami2montreal 
I have done some repacking on boats before. Long time ago. It can be done while in the water. I would borrow or make a coffer dam to go on the outside of the shaft and create a seal against the bearing housing. Have a good pump ready to keep up with the water. Or get some air bags and raise the stern high enough to get the housing dry. It would be smart to get a local mechanic to help and maybe a lift.
My 2 cents for what it is worth. I know they can be done on the fly. You pull out the last ring of packing and add a new one and tighten. Make sure you cut the packing clean and diagonally so it seals when tightened.
I just repaired the manifold so that packing is going to remain on the to do list for now. A mechanic offered to do it for cheap but I have to head south if I ever want to get to the bahamas. It’s not leaking enough to be a problem.
Remember sinking slowly is the lesser of two evils
I did not start the engine for two weeks and the packing stopped leaking completely. While it’s not good to keep the engine still for too long, it took me three tries to start it again, at least I know that if I leave the boat it will not sink.