plus a few people I know are always having problems with theirs
Considering the sheer number of people that have iPods, I wouldn't worry about a few people having difficulties.
I have a Sony Walkman. (one of
these) and although I really like it as a player (good battery life, quick recharge, AC adapter actually included (Apple, you suck), and cool display that, well, just look at it) but the software that it needs to work (think Sony iTunes) sucks balls. It's slow and often unresponsive. The music is encrypted when it's on the player so that you
need their program installed to even access the music on your computer, and to top it off, the program won't remember you have
already encoded that MP3 to ATRAC3 and forces you to re-encode it (you now have
two encoded copies of the song at the same bitrate and everything) if you want to re-put it onto the player, say, after reinitializing the disk. Also, it should be noted that while the player can tell me each song I was listening to back in April, it can't display the time (which even their cheap flash drive models can).
I like mine alot, but I have to tell you to stay away simply because Sony should know better than to have such poor software (and it is bad, trust me).