On October 11, 2017 at 20:39, tweeterguy said...
My take: he has a cabinet with a wire pass through hole from the factory or previous installer; it’s too small of a hole, he wants it bigger to get more cables through.
Always cut 2" holes for wires. Straight three-prong plugs require a 1 1/8" hole (IIRC), but if you cut a 1 1/8" hole and then someone runs a couple of cables through the hole, you'll have to unwire the entire system to remove that power cord. So cut 2" holes.
Then if those holes need to be enlarged, I push the pilot bit against the side of the hole and take a bit more wood out of one side of the hole.
My idea: have some monkey hold a board on the opposite side than you are drilling. This will give your pilot drill bit something to bite into while the hole saw starts to do its thing.
You'll need an especially long pilot bit for that, but sure. The other approaches don't require anything special.