Making some headway. Here are the highlights:
1) It took a while, but I achieved even coverage with the dye, especially around the edge of the headstock. I learned that the process is more of art than a science. I tried some Minwax water based pre-stain wood conditioner from Home Hardware but didn't notice any difference. Armed with 180 and 600 grade sandpaper, I sanded the tough spots with the 180 and then applied the dye, working it in with the 600. This did the trick and I'm happy with the colour and the coverage.
2) I returned the Valspar clears gloss black I bought from Lowes in favour of the following (from Hone Depot); Varathane Satin Clear for the neck, Zinnser shellac base primer/sealer for the back of the headstock and heel, flat black paint (rather than gloss) and gloss clear.

3) Started the pickguard lamination process by first cutting out a piece. I used a jig saw with a fine blade that's used to cut thin metal sheets.

Then heated and clamped to headstock.

I then drilled a hole for access to the truss rod, scuffed up the surface of the headstock and plastic with 80 grade sandpaper, glued and clamped.

The plan for today is to trim the excess plastic, finish the edges, touch up the edge of the headstock (with dye) if necessary, and apply the satin clear.