Mako, I suppose I could have tried something like that...but what you don't see is that, for most of the run, it is rare for two cables to run together for any distance. Also, ther are two completely different electrical systems (240/120 and 480/277), and I tried to separate them as much as possible, to reduce the chances of wires getting mixed up.
Gideon, your comment, while similar to some I'd heard before this job, highlights the importance of getting the mfr specs. In this case, the specs made clear that I could make a small hole ANYWHERE in the web- which often became important, as I dodged around pipes, ducts, and the like.
This also relates to Mako's comment....not only is it a lot easier to drill a small hole, the specs were a lot less restrictive.