I bought my 4GB iPod Mini about 6 month ago and here are various things I hate about it.

1. The price.
   Value for money is simply off the scale. You can get a player with similar features for half the money.
2. The headphones.
   They are white… yuck.
   They are to big for my ears … so they hurt after a while.
   They sound horrible. They have a lot of power in the bass, but the heights are barely audible. This is ok for modern Techno/Drum’n'Base, but not for the music I listen to.
3. The clickwheel.
   It doesn’t work if temperatures are below 10C/50F (Read: winter).
   It doesn’t work above 30C/86F (Read: summer).
   Sometimes it just doesn’t work at all.
4. Playlists handling I - Navigation
   The “three clicks to every song”-myth. I have about 400 different artists on my iPod, so when I want to listen to Madonna,
   I have to CLICK (1) Menu, CLICK (2) Music, SCROLL (1) Artists, SCROLL (240), CLICK(3) Madonna, CLICK (4) All, CLICK(5) “Song”.
   Even if I count each revolution with the clickwheel as only on click, I still end up at around 20 “CLICKS”.
   My car radio (empeg MKII) has a user-definable playlist structure, including hierachical playlists. That makes it so much easier. With over 800 Artists I need only 8 “CLICKS” … worst case!
5. Playlist handling II - Podcasts
   Maybe I’m too stupid, but…
   When I want to listen to a podcast in my car all I do is to go to the podcasts menu entry/playlist and click play
   and it simply plays the oldest not fully played song/item and starts at the last position I listened to.
   With my iPod I have to remember where I left of.
6. Reencoding.
   Why oh why?
   When I load music from iTunes onto my iPod, I want to reencode them to 128Kb/s MP3.
   The 320Kbs is simply to big and not noticable with the poor headphones anyway,
   but stupid iTunes won’t let me do this
   You can only reencode to AAC … and that’s neither what I want, nor what I need.
7. Portability.
   Why do I have to decide if I want to use my iPod from MACOS or Windows ?
   I got a Mac at home and one at work, but when I’m on the road there are only windows systems.
   So what now ?
   Stupid.
   My car-radio works with macos, windows, linux … and everything else. At the same time!
8. The off switch.
   The what ?
   Exactly. Where is the freakin’ off switch ?
   Everytime I get out off an airplane an pull out my iPod I find the batteries empty, because someone/something touched the button and it was playing the whole time.
   Add an hardware switch and that problem is gone!
9. Firewire
   Need I say more ?
10. Last, but not least:
    The display.
    Too much (useless/uneeded) information, while the important info (e.g. title and artist) is written in 5 point font.
    I have really good eyesight, so I can read it from a foot away, but other displays - with the same size - are readable from 10 feet away.

Would I buy one again ?
I guess not…