Whenever I need to drill a hole into the end of a long workpiece that won’t fit on my drill press, I use my doweling jig instead. I clamp the jig to the workpiece and drill the hole as deeply as the jig will allow. If the hole needs to be a little deeper, I take the jig off and use the “starter” hole as a guide to continue drilling. In fact, I used this technique recently to install a post-type swivel caster on a table leg.
– Gary Storme