The most annoying time I ever lost power was when I was in the Army. Being a nerd, I worked in a suitable nerd field while in the military, though among my list of talents, generator repair is usually near the bottom, right above complex surgical techniques.
The basic problem was simply that, someone failed to follow proper operating procedure for a large piece of equipment. Suddenly removing the power hungry system from the grid caused a number of generators to overspeed, followed by the malfunction of the one generator that I was at least partly responsible for. Unfortunately, for some reason or another, our equipment would only function if this specific generator was running, meaning it needed to be repaired - and we were informed that because it was a non-standard piece of equipment it would take weeks to get a contractor in to repair it (army mechanics are only capable of repairing things that have instructions written in an Army manual - it's almost a law).
Thus, it became apparent that if I wanted air conditioning, or anything else that required power I was going to have to fix it myself. Using a Leatherman Wave multi-tool, a few screw drivers and a few wrenches (and at one point a sledge hammer and an axe), along with near electrocution on at least one occasion I managed to get it back up and running - a mere 20 hours after the event took place. During that time, the air temperature was sitting well above 110 F, and I can only imagine what the ground temperature was (likely over 130).
All the other times that power goes out seems like a minor annoyance in comparison because the discomfort was immediate and quite profound.