I don’t have any interesting haircut stories to share (but am enjoying reading those who do!).
For financial reasons, I cut all of our boys hair (but not my own). I bought a $30 Wahl set at Sam’s a couple years back and it still serves us well. I read the directions, followed them, and haven’t given a bad haircut–yet. I cut their hair about once a month. I’ve already saved way over $500 (might be closer to a $1000 by now).