When I bought my first iPod used for just under $300, I thought it was a bit expensive. But it worked, and it worked nicely. But, after a short period of time, I reallized that my HD had issues. The 40GB drive holds a lot of music (I actually only *own* about 12GB of music), but, it had it's troubles. I'm sure this isn't a new story to anyone, but mine would tick, whine, and start this process all over, while NOT playing music. If you slam it REALLY hard against a solid surface, sometimes it comes back to life. Sometimes, it would do nothing and need to be reformatted, or "updated".
So, after months and months of slamming the iPod to make it work, I traded my useless (yet, reliable) PSP for another used 40GB iPod. Which worked *way* better than the first one. Of course, the love affair was ill-fated, as now my "good" iPod is displaying the same characteristics as the "bad" one.
I love my iMac. I love my iPod(s). They work fantastic. But the iPod is also a source of endless frustration when I'm trying to actually USE it.
I can't think of anything else that I've had such a strong love-hate relationship with before!