I would build up the red first to get it even and then the black .
Sounds like it could be a plan. As far as i can tell, the bit that is worn, for lack of a swear word, has had no mylar on it at all.
That sounds like a pretty good plan to me too. The only other thing i could add would be to clean up (lightly sand) and prime the bare wood first before you attempt any painting. And maybe some spot putty after that to get it nice n level if needed. I use K&H brand acrylic primer/filler for doing this, (bought from Supercheap Auto or Repco, etc). Its sold in spraycans, so some masking off is needed (Occasionally i'll brush the primer on by hand, spraying some primer into a small container or the lid off the can). sometimes the primer/filler is enough on its own without using spot putty if the wear is not too deep.
Hope this info is helpful!!
Cheers.. Mitch