You're forgetting that this is Newgrounds. Anything that might be marketted well or seen as a "new and cool" thing is usually shunned if it isn't taken under the wing of a highly-respected user and positive light is given to it. (Also, Maddox has said he doesn't like iPods. Oh no, they can't be cool anymore!)
Honestly, I've never had a problem with my iPod. I have a Black Faceplate 30gig iPod Video, and I love it. Granted, I've only had three and a half months to fiddle with it, it's been well-worth the $280 it cost. I did my homework while searching for a good mp3 player, and found that the only one whose aesthetic and economic designs fit my needs and wants was the iPod.
I'd assume the majority of peoples' anti-iPod sentiments stem from irrational brand trust or distrust, not from actual comparison of price, quality, durability, and stability. I guess it's all in what peoples' needs are (mine were specific in that I wanted to be able to have a large portion of my musical library available with me while working, idling, or travelling away from home, meaning that I wouldn't have been able to sacrifice storage space to keep away from Apple).
I've had no trouble with the headphones, aside from losing one of the little black foam pad jackets that slip onto the earbuds, and the transfer rate of songs is a perfect pace for me to grab a drink while it's updating.
As for songs and file associations, I've had no trouble. My music collection is comprised mostly from ripped CDs and songs I've shared between friends. I've never used the iTunes Store to purchase songs, and I doubt I'll ever have to.
Note:
" I'd have responded to the other posters in this topic, but it seems as if they're all too deeply self-involved to hold an intelligent discussion about the merits or demerits of the devices without just blatantly smearing the brand name or giving baseless arguments.