I wouldn't think you'd want to apply the vinyl before you drill the holes/slots.
Vinyl + Drill =
FAILYou're almost certain to get tearing and a ragged edge.
The best way I found for long straight cuts is to apply the vinyl, turn the piece vinyl-side down on a cutting surface, then cut from the underside of the vinyl using the vertical edge of the wood to guide the flat of the blade.
For tight turns and small radius cuts, you'll want to cut in from the vinyl side.
Like Rikitiki says in the
Side Art Install 101 thread videos, take your time and use a fresh blade.
You
did watch these videos, right? There's nothing like seeing a pro in action to figure out how to do something.
Scott