Welcome from your neighbor to the east, Paul! Glad to have you with us! You're definitely off to a good start. Let me just add you may be making more out of the drilling process than is needed. I've spent a lifetime drilling holes, and all this takes is a good sharp bit (regardless of angle), some machine oil, and a little muscle! No need for the drill press - just center punch the hole, brace your smoker (or lay it on its back), and power through it! No biggie, just don't be shy! With a 5/16" bit, you're not likely to break it with a little brute force.
Sorry, can't help with the toggle switch question, as I don't have one. Bypass all the way for me!