Despite the iPod being great, iTunes has numerous bugs which cause some annoyance. By numerous, I mean crippling. This is definitely a problem with iTunes and Windows Vista (my primary OS) not getting along. The problems ranged from bad syncing to blacked out displays. However, after some random clicking, countless reinstalls, and display updates, I was able to fix the problem and am very happy. The iPod holds my entire collection (+ some music videos) easily. Additionally, the sound quality is decent and the interface is great. Plus, I am cool now! 
However, I’m not here to write a review - so many people have already done so. Who knows? I might even contemplate getting a macbook… so long as Apple supports its own software on its own devices.
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Ever thought about the fact that it is vista, not iTunes, which is buggy?
/gradster(1)
Vista may have some errors and iTunes has some errors. It is the combination of the two which causes problems. However, it is the software creator to ensure software works, not the OS creator. Therefor, since other programs work fine on Vista, I am led to the conclusion of iTunes being the weakest link in the equation.