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i would have to say 3rd gen. Although i dont own an iPod Classic, i have used one, and i do own the 3rd gen.

the 3rd gen iPods are just so cool with the all touch, lit up red 'buttons'. also no risk of damage on the buttons since there aren't any movable parts, except for the hold switch. :D

ahh such fond memories with my first iPod :p i used it for a good 3 years before needing to get a new iPod
 
My first iPod was a 20GB 3G and my main current one is a 160GB classic.

The classic is better in every aspect apart from one. The lack of firewire is a real pain when you first load up your music but isn't that much of a problem after that.

The battery life on the 3G was really poor, it wouldn't last a full day at work while the classic will last for the whole working week :eek:

Add to that it has a bigger colour screen, huge storage capacity, it's thinner than my old 3G and the classic was £70 cheaper.
 
I now have a 15GB 3G with a new battery (which lasts much longer than the original) and a second hand 30GB 5G. The 3G's touch buttons are much nicer, but having colour and bigger storage means I'm waiting to find a use for the 3G. I do miss iPod Linux, which for some reason I can't seem to get onto this 5G.
 
When the click-wheels first came out I preferred the navigation buttons on my 20GB 3G and couldn't see how anyone could stand to use a click-wheel.

(Cue two years later when I was given an iPod Classic)

All I can say now is that I don't know how I ever lived without a click-wheel. Maybe its just me, but its alot easier to navigate without looking down like I had to do with my 3G (When it was on my belt it almost always took me four seconds to feel for the pause button vs. less than one second on my Classic). One thing I still miss about my 3G is the way that the buttons lit up. That was one cool feature...
 
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