I started back in on this project this weekend, and got a VERY good tip from my cast iron forum-
They advised putting the match safe in a plastic baggie, then putting in the Jasco paint stripper and sealing the bag. This did two things. First and most importantly, it kept the Jasco from losing strength when it comes in contact with the air. Second, it enabled me to direct the Jasco gel to the areas where it was needed and it holds it in place instead of slipping off the piece. The paint came off with very little effort after that.
The naval jelly worked great for getting off the rust in short order too.
So here is the match safe, cleaned and freshly oiled: