It certainly can be.
One of the more difficult flyovers I led was for 2008 Air Force Week in LA. We held over the Rose Bowl. Because of LAX airspace, our initial inbound heading was roughly south, with a pylon turn to the west around downtown IVO East Los Angeles, for a westerly run in. Although the video looks like it is bright, it wasn't. In fact it was post sunset (we had a waiver). The downtown lights were very bright, and the Coliseum lights are pointed down and in, and don't show up until the last portion of the run in. Staying below LA's Class B with the huge amount of lighting in the area added to the difficulty.
This was 12 years ago, and yes, GPS existed. But due to the non-linear IP-to-target run, the intricacies of SoCal approach and the potential flex of the Anthem, it was quite dynamic. And we are flying the A-model, not the C-model with whatever bells, whistles and HUD it has.
We did extensive route study, timing contingencies, etc... and we trained like it was a "GPS-degraded environment". I suppose we could have laid down 99 waypoints on the curvilinear route we flew... but we didn't. We used a Sectional, LA TAC chart, and some aerial photos.
Once the flyover was done, due to LAX congestion, we managed to get sequenced into the LAX traffic flow, did 2 night wing landings, well after sunset, in black jets, to 25L. Everybody involved in the evolution, including an F-16 pilot, TPS graduate, and a lot of high-time instructors, felt a good sense of accomplishment. The intricacies of completing the flyover included getting the formation to EDW, and getting the jets safely on the ground at LAX's FBO. We knew we were going to break a number of rules to get it done, and we got the waivers from HQ so we could do it. ALL OF THAT COORDINATION is part of making it successful... not just the last 10 miles of the run-in.
Anyone can scoff doing flyovers if you want. And maybe my geekery combined with the fact I don't drop bombs gives me no "real world relevance". But I've done shitloads over the years and found ways to challenge myself on all of them. And I'm a better pilot for it.