I cannot believe you guys just convinced him to buy a older iPod. The music will come out the dock - which means it doesn't matter what audio chip it has. Keep the 16 GB Nano, it really is a great platform!
Agreed. iPods are pretty sturdy, on the other hand unless you are a serious audiophile there is no point buying a used 5G iPod as opposed to the current classic. Given that you've not even read up anything about lossless files vs the many other formats I doubt you are an audiophile.
I really, truly don't think you'd be any less happy with a current gen iPod. And if something does go wrong you have the warranty.
Honestly sir, you are making way too big of a deal out of this. I am the same way though, I like to do my research before I buy anything, but you really can not go wrong any iPod you choose (providing it offers you all the space you require).
I agree with everything that post said. The nano would have done you fine with 10GB, if you have dvds too then the extra space needed makes the classic the one for you.
Why don't you load everything into iTunes and see how much space it takes up? Then just buy the iPod that'll fit it. Job done.