Thanks, Frank. I will probably do that. And, if I don't get any further suggestions, will probably try the procedure I outlined above (installing top bushing, marking hole locations, etc.). I would guess for the depth the holes need to be, most wood would be reasonably flat enough.
Lots of advantages to this idea. It fits most sizes (I guess you would need a smaller one for smaller and shorter bits) . Its doesn't cost much if anything. It wont ruin any drill bits. And you can see where you are drilling (most important advantage to me).
After re-rereading the OP's post, he brings-up a pretty good idea:
So, the next time I'm around the drill press with a nice chunk of thick aluminum block, it sure wouldn't hurt to take a few minutes and drill a series of commonly-used sizes of holes just for this purpose in the future.
I usually use a pin vise to drill those little screw holes for tuners, truss rod holes, etc. There's a big selection here:
This one looks like it's pretty versatile:
What you get depends on the size of the drills you need to use.
I'd forgotten about the "General Tools" drill guide in a pinch. If a drill press was unavailable and someone just had a portable electric drill to use, this gets the job done. It'll adjust to 90-deg or almost anything else.
Additionally, the "vee" blocks on the top of the base make it suitable for drilling straight holes into a dowel or piece of pipe. I think they're around $30 at Lowes or Home Depot...
If you're talking about hand tools for drilling holes I have some for you;
( My apologies for the picture quality. It's my, not so great, cell camera. Quick but not so great.)
The picture shows my "cheap screwdriver set" chuck with a short, cheap, bi directional handle. Both are from different sets but together make a fairly decent pin vice and I can extend the shaft if I need to.
The others are old exacto handles which, for some reason that it beyond me, I seem to be collecting. I drilled the first two for different sized bits. They don't hold as well as a chuck, probably because there is no taper to their grip surfaces but they do well enough for hand use.
The last two are a small, homemade saw for long distance cuts and the standard Exacto micro saw blade. I didn't like the bulky handle that came with the micro saw so I drilled out one of my old billet handle for a slimmer handle. It works very well.
I also, sometimes use an old T handle from a tap set and for small, shallow holes I sometimes just use my fingers.
Thanks, everyone. A lot of information to consider, and a lot of alternatives. I appreciate all the responses. I guess there is definitely more than one way to drill a (small diameter pilot) hole.