I'm pretty good with technology compared to the average person (or at least, those whose job description does not consist of spending their whole lives in front of a computer), and even I managed to wipe out a lot of my iOS data when simply switching to a new computer (thankfully I had done an iCloud backup in anticipation of things going wrong and was able to restore. Still lost one app's data in the process, for some reason).

We definitely have a long way to go, although I think a lot of the stuff we put up with is also due to accommodating external forces like backwards compatibility, pressure from the music and movie industries, etc.