The nut problem was related to the spur slipping and taking the outter plate and washer with it. Cleaning the plate up with a dremel sanding drum, as well as putting a second washer on it, with grease between them (to create a slipping point), as well as some red high-strength threadlocker fixed the issue.
If anything, the only real issue I've ever had was the spur being slightly off-center, causing a variable 'gear lash'. Just enough to be annoying, not enough to kill spurs.
It does kinda sound unrelated... but if the spur is too loose in the slipper plates, that could cause overheating and melting of the middle area of the spur... Which could warp the gear, and cause some wobble.