Hi Tim,
I don't know how George does it, but I lay the cutting edge on the edge of an oilstone (medium) with the drill parallel with the top face and canted out sideways and stroke it along the edge a few times - this gives you a flat (George reckons 1/32", I usually go 0.5mm - 1mm, same effect) on the edge at right-angles to what you're cutting, kind of like a zero-rake tool for turning brass, so it "scrapes" the material rather than digging in like a positive-rake tool.
My favourite tip would be transfer screws, as a lot of people don't seem to have heard of them!
To transfer the location of a blind threaded hole to a covering part, turn a 60-degree point on a short length (or a bunch of 'em) of thread (I find the end of a capscrew works well) then grind a couple of flats on the pointed end to grip and turn it with. To mark the hole's location screw it/them until the point's about 0.020" / 0.5mm above the surface and position the covering part - a couple of thumps with a malllet and you'll have nice neat punch marks in line with the threaded holes - simples!
This works really well for fitting chucks to backplates - a hell of a lot quicker than trying to measure the mounting hole PCD off the chuck and mark it accurately on the backplate
Make up a bunch in your preferred sizes (I have a half-dozen each M5 - M12 and a few UNC/UNF and Whitworth/BSF) and store them in the little boxes taps (once broken) come in (ideally the taps for the thread size) and you're good to go.
For *unthreaded* holes it's a bit more difficult - you'll need a good fit, but not so tight you can't pull 'em out by the flats - and yes, I've had a struggle a few times! If you leave 'em soft you can always dremel off the point, drill and tap and then pull/lever on a screw threaded in - desperate measure given away for free!
Dave H. (the other one)