For what it's worth, I have called an electrician to resolve this, but that doesn't mean I'm not curious as to understanding what could be going on.
I have an older home, built in the early 70s, so it has seen quite a bit of remodeling and both DIYers and electricians throwing Romex all around the attic. While trying to troubleshoot this on my own I found a plastic junction box with splices, pigtails, and wire nuts. Whether this poor craftsmanship has anything to do with the problem, I don't know.
At any rate, one afternoon an electrical outlet that did have a fair bit of electronics connected to it (computers, monitors, a laser printer, a Juniper switch) stopped working. I moved the equipment over to a different outlet in the same room and got back to work. Unbeknownst to me at the time there were three other outlets that were out, all in the same vicinity but not in the same room.
Fast forward to today where I got out a non-contact voltage tester and went to the four outlets and confirmed that none of the Hot lines are registering. I also confirmed with a Fox & Hound that these outlets are on the same circuit or at least their Hots are connected, though I don't know what other outlets are on it.
So my question is whether there's anything else I could do to troubleshoot why these four outlets are dark? Any speculation as to what could be happening? Once the electrician figures it out I'll post an update.