I liked the music one.
(I thought the other one would be funnier if it was Y10K problem. Y3K shouldn't be any more of a problem than Y2.1K will be, because I don't think many people hacked Y2K by going to 3 digit years...)
2038 is the other big one for unix folks, maybe.
The other subtle thing about music is how scales in general aren't as simple mathematically as they look. (In short, to get proper sounds, you need to use a bit of calculus, not just algebra). http://www.jimloy.com/physics/scale.htm
explains some of it ... i remember other tales of Bach torturing his organ tuner by playing those combinations of frequencies that sounded terrible.
You shouldn't be afraid to do stick figures. While it's not as easy as it might look, it's also not all that hard, and a little practice can go along way.