On Dec 12, 11:16*am, BrianSiano wrote:

The project requires drilling pilot holes into the ends of boards that
are roughly 30" long. You can see that this can be a problem even with
a floor drill press.

I'd consider making a doweling jig (just an L shape with some
hardened drill guides pressed into the short leg) for this kind of
thing,
clamped to the board end. Just hand-drill the holes.

It can take some careful setup on a good drill press to make
the jig, though, and you will need to find a source of
suitable bushings for the drill guides.