A year and a half ago I placed high in a bowling tournament and got enough cash to buy an Ipod. What I bought was an Ipod 40gig clickwheel. Since the day it arrived it has been a complete problem child, and knowing what I know now I would be very hisitant to buy another one in the future.
I am a PC user, though according to the Apple propaganda this should not be an issue. I use my ipod heavily--when it is working--listening to very large audiobooks and leaving it running for hours at at time. Still, this should not matter. I keep it well protected, the battery well charged, and it gets better care than my laptop. Still, I have sent it to Apple 2 times now and just ordered the box for time number 3. All for the same problem: hard drive failure. In fact the Ipod I have now that just crashed on me is one that I got as a replacement only a couple weeks ago.
Apple touts itself as a crash-proof manufacturer. Don't believe it. They have a lemon in the 40gig clickwheel, they have to know it, and even their tech support aren't allowed to admit that it is a design failure. According to this study the 40gig clickwheel has almost a 30% fail rate, with some reported problems being repitious. Notice that they no longer put out a 40gig version.
I paid the extra $60 for the Applecare plan, which is going to buy me another year of replacement Ipods, but I fully expect them to fail one after another until Apple gives me the finger and refuses to replace it anymore (this Feb).
...and when that day comes the odds of me buying another Apple product are slim to none.