As far as I know, the big issue with the iPod Classic is the Hard Drive. The Hard Drive can fail if the iPod is extremely used or beaten down. As a buyer, you are fairly protected by eBay and Paypal, so if you did get ripped off, you would get your money back. It would be a hassle though.
Within the audiophile community, the iPod Classic 5.5gen is considered to be the "best" iPod due to its better DAC. The newer iPod classic supposedly sounds worst. Personally, I own a iPod Classic 5.5 generation 30gb, Zune 30 gb, Sony Walkman E 4gb, Sony Walkman A 16gb, Zune HD, Sansa Clip Zip.In terms of sound quality, I would rank the iPod second to last. The Zune HD IMHO sounded small and weak without an amp. I would say the Zune 30gb has the best sound quality, followed by the Walkman's. I bought my iPod Classic off craiglist for $75 and used it for about 4 months until I switched to the Walkman A series. It is pretty beat up, but it works fine. You should know that Apple has recently "improved" its docking connectors, so your iPod Classic would most likely not fit with new iPod Speakers that are currently being produced. A $29 adapter is available. (If all of this information is old news to you, sorry
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Amazon is selling the iPod classic new for $230, and Amazon Warehouse Deals (where Amazon sells open box stuff) is selling it for $200. If the iPod is for yourself, I suggest buying it from Amazon Warehouse Deals. 99% of things I have bought from them have came in new condition, with only the box being damaged. Warranty, however, may not apply to those items.
Best of luck on your audiophile journey!
