So, here's what I've done, now that I have enough info as to what I have:
1. Removed the cover to the gear side of the windlass, and the gears looked great and all turned without issue.
2. Remover the cover for the motor. Pulled out three of the four brushed (that were accessible) and they looked perfect. Cleaned and reinstalled.
3. Loosened the nut to the gypsy free fall, and once loose, it turned easily, no issues. Couldn't get the gypsy off because I couldn't get a key to line up with the slot.
4. Checked voltage drop from foot switch, to ground and got a drop.
5. Wired a temp 10gauge wire from the ground off the motor directly to a solid ground under the lower helm, and didn't work.
Running out of ideas.
Thoughts
(also posted on other sites)