Why I wont buy another iPod

I've had a first gen 2gb iPod nano for just over a year now ... yes I was one of those people who was sold the moment they saw one, although to be fair I was looking at buying a new mp3 player anyway so it wasn't a total impulse buy.

Anyway, about 1 year later I think its time to upgrade to a higher capacity device. But will I get a new iPod? The simple answer is a "no". Here is why:

1. iTunes. I'm not talking about the shop (I've always used AllOfMP3!), I am just talking about the software. Its the biggest heap of shit I've ever used. It is slow, bloated, buggy and most of all its crap at its main purpose of loading music onto the iPod! For example imagine you had 100 albums you want to copy to your iPod, but only space for 50; does iTunes copy over the first 50 complete albums? No that would be too sensible - instead it copies over a random selection of tracks from all 100 albums...why?!!?!!
2. It is no longer "cool"...I'd be tempted to say that it was "cool" only for about 6 months before people actually knew what it was, but that is perhaps another story...
3. Despite everyone ranting about how well designed these things are, you cant unplug the data-cable without having to unplug the headphones first because they put the plugs too close together.
4. The data cable shell breaks after a few uses.
   
5. The Hold-Play-To-Turn-Off implementation is irritating; it sometimes takes several attempts to turn the damn thing off.
6. The so-called gapless playback is pretty random. An album will be gapless one day, but not another?
7. The latest firmware has changed how the device works when skipping tracks. Now it seems that to rewind a track I need to press the back key 3 times, even if I am only one or two seconds into the track: once to "wake" the iPod up, second to rewind the track, and third to actually go back. I am convinced that this never used to be the case - now it just feels like its not responding or broken or something when trying to go back a track.
8. Its really fragile and prone to scrapes and dents and all sorts of injuries despite living in a case all the time.

So there we go. Rant over. Basically I have been pretty disappointed with it all, particularly the software. If they were hoping the iPod would drive mac sales then they should have spent a lot more time working on iTunes because at the moment it just leaves a bad taste as it were.

What will I get instead? No idea to be honest - the zune is looking interesting. Maybe I will get one of those if it can update its music wirelessly (i.e. not just sharing tracks with others wirelessly).