Thanks for the great Tutorial. I did the same thing with a 1950 Williams Lucky Inning. The playfield was so badly separating that I had to create a new board, drill holes, re-insert inserts and then paint layer by layer.
Mike

Before ...Just the top layer of veneer with the black line tracing on top to make sure it lined up correctly.

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Then mask, paint, paint, Done!

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If you're asking me.
1. Scan and get that black ink outline. Helps keep everything in line.
2. In my case, the ball players were a little too detailed for my cutter. Even had a friend try on his machine and some of the super fine detail got lost. I think next time, I will create water slide decals of these super fine details and apply over the general color, in the case of the ball players, the decal would be on top of the white for the uniforms.
3. I used Golden high flow paints. I used the color matcher app Golden has on their site as I was trying to keep the machine looking old as that is what the customer wanted. I think I used 5 colors just to make the dirty white.
4. make sure to try out your masking film before you plunge in. I bought several kinds before I settled on what I used.
5. As stated by dr_nybble Spray light coats and build to your final color. Once I had the color I wanted and before I went to the next color I heat set the paint with a hair dryer. This helps prevent the masking from pulling up set paint when you do another color. Remember that once you heat set it, you can't wipe it off with water. It has to be sanded or scrapped off. I had to do that in a few areas were I had over sprayed.

Hope that helps.
Mike