Help with headstock inlays

I'm currently working on the neck for my guitar that I'm building. I'm going to paint the front of the headstock black to match the body. I also want a one piece inlay on the headstock.

Just wondering which way I should do it? Do I recess the cavity, tape it off and paint the headstock or do I paint and then recess the cavity, and if I do it this way is it best to do it over tape to prevent scratching the finish.
Following this video: 

Many thanks for any help,
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