Yeah, if you've got that access to the stuffing box, do it now. The gore-tex packing is nice in that, after adjusting once or twice, you probably won't have to adjust again for a long time. The flax packing needs adjustment every now and then; a 5 minute job on a PS190 but quite a bit more for us.
For the cutlass bearing, I'd pull the stuffing box hose off the shaft log, and check how much play you can feel in the transmission side of the propshaft (only the cutlass bearings and your hand should be supporting the propshaft). A little bit of play is fine, a lot of play isn't. If the propshaft wants to lean against the side of the shaft log (strut is bent and needs to be fixed and cutlass bearings will be worn to one side) or if there is a lot more play left-right than up-down (or vice versa), I'd swap out the cutlass bearings.
Things are looking real good there. Hope you're on the water soon.
1998 Maristar 200VRS