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I prefer KISS to finicky parts in inaccessible locations, so I'd ask just how bad the stuffing box is, and whether gore-tex packing in a conventional tube might not be preferable to a PSS system. If you go with PSS, those set screws are the reason that Loctite cleaner and threadlock were invented, invest ten bucks in making sure they stay put.
The toilet wax rings work very well but if you're taking out the whole tube and dropping the shaft, that's a lot of potential for getting stuck and having the boat ashore in case you get stuck overnight would be a nice idea. Or at least, have a good set of damage control plugs available so you can literally hammer in some protection if you need to leave the boat with the shaft out overnight.
If the profile of the boat's bottom and the dockside/shore work out, you probably can weight down the bow until the stern comes out, or use floats to raise the stern out. From 15-gallon heavy plastic chemical barrels (free "garbage" behind photoprocessing labs and some food packers) to used 55-gallon drums, you can often get some kind of flotation for free. Tied together, slipped under the hull and hauled forward, they can raise the stern but...if you can find someplace to just haul the boat and put it on stands, that might be the most effective thing to do. Certainly the most "relaxed" way to work when the job is a first-timer and may get complications.