I will never drill my bars for anything especially anywhere near the stem. I've lived through to many fork/steerer/stem/fork failures already and I tend to ride good equipment I like until it dies. So I have no advice there. I run my housings along the front of the bar under my second finger joint when I am holding the bars by the tops, like during easy and seated power climbing. I also wrap my bar tape from the bar ends so it is an easy matter to unwrap them, mess with cables or lever placement and re-wrap.
So ... "Apologize if this is I just want my steed to be fast, sturdy, maintainable, and looking a bit sharp" ... I think I've covered your criteria.

Ben