One-man rigging aids - is the electric up/down control worth it?

Herb, I think Evan asked a valid question, seems like you gave a valid answer. I see no need to "remove gears" to test a geartrain failure issue.
If a fine pitch (as you indicated), likely basically no issue.
Thick grease may negate an issue on a coarser pitch.

Unless, of course, a major earthquake that rattles bits around......then, what a wing rigger when it fails is doing is likely a moot point.... ;-)