As far as the paint adhering to the surfaces, the cloth sleeves(if used) around the wires, the insulating paper, and the wood wedges(if used) that lock the windings in the slots all soak up the paint somewhat to increase the insulation around the wires. And, as you say, "glue" the parts together to keep them from shifting around and chafing.
I've also damaged windings . Sometimes, not always, you can carefully pry back the wires(if they're not burned-up) in the damaged area, insert pieces of the insulating paper to re-insulate the wires, and repaint. Motor shops will give or sell you the small amounts of paper as well as the insulating sleeve material, if needed. They also would be a good source for the insulating paint.
You're right. It is a chore to do this. And, it sounds like you can't wait to get back on the road!