Doogan, question for you -- what's your painting setup look like? In my keycap flocking thread (see my sig for the link) I put mine on skids to hold them down and manipulate them. I'm not painting the way you are, I'm really just sanding, and priming, but I'm pretty happy with my setup. How do you manage to keep the caps from moving around?
I don't know if I will be able to describe it very well without photos but here goes.
Step 1 - I sand the keycap first with 600 grit and then finish it by wet sanding with 1500 grit.
Step 2 - I position the keycap on a makeshift dowel so I can keep it from moving or falling over while still keeping it off the ground. Which means I can turn the keycap without having to move the direction I'm spraying.
Step 3 - Once I am done spraying the keycap I take it indoors (so it doesn't catch anything) and set it on a makeshift stand keeping it level.
Step 4 - After coating it a couple of times a let it sit overnight so the paint has time to cure before I hand paint it.
Step 5 - After I spend way to much time hand painting it I let that paint set for a bit. I then layer it with a lacquer spray and let it harden for a couple days. Then it is ready for use.
I can upload pictures later of my makeshift stand and keycap dowel fastening thingy ma bobber. Everything but the actual spray painting is done within my house.
I read through your flocking thread and that looks awesome. Makes me want a purple velvet spacebar. I think you would benefit from being able to paint your keycaps off of a surface so you don't have to cut off the excess flock.