I fixed up a set for my '37. Mine are black back ground with white letters so it was not to complicated. For the back ground I powder coated them gross black, so in case I made a mistake, the white would come right off with out taking off the black.
For the letters I used a ceramic based glass and dish paint I found at the local craft store. Sort of like a liquid powder coat, once dry, you bake it for 20 minutes and it smoothed out and got a nice shine to it. The hard part was hand painting them, not really that hard, just took a lot of time.
Right up close you can see the flaws, get back a bit and they look just fine. Check the web for license plate painters and restorers, the prices may scare you in to trying it yours self!
Joe