Updating software annoys me.
I like Janie's Red Queen metaphor, a constant chase that gets nowhere, but you have to keep up. Updating software is utterly pointless if the old stuff still works, but if you don't then everything breaks.
If you give a person a program, you will frustrate them for a day. If you teach a person to program, you will frustrate them for a lifetime!
I'd rather like to have one of Vernor Vinge's "mature programming environments", where programming isn't a matter of boiling the ocean by starting over, or fixing code to match new APIs, but finding the parts you need and gluing them together with new code in old, ancient, centuries or millennia-old APIs that Just Work. For quite a while, the NeXTstep/Mac environment was like that, 30-year-old NS programs worked fine. But now everything is broken again.