Yes. I am planning to try some different headsets and earplugs, even though I already tried 3 high-end sennheizer and 1 high-end Sony. No significant improvement.

To tell you the truth, what I am honestly thinking I should really do is sell this iPod Classic on eBay to some iPod fan, since there are many, and get a Microsoft Zune, which I am learning more and more about. I am so mad with Apple as of now, that probably this makes me look at the Zune as a better device than it actually is. However, most review talk about extremely good audio quality for a portable player. I guess it is easy to beat the iPod in this.
Zune, however, does support lossless WMA files, which is extremely appealing. It has a bundled FM radio, and the iPod does not. It comes with WiFi (and iPod does not), a larger and nicer 3.2" display than the iPod, and it does have a number of nice accessories (alarm clock, docks of all kinds, etc.): not as many as the iPod's, but those that I need.
I am not even mentioning the FM-related features, as I am not really interested in tagging and downloading music on line. I just want to buy my CDs, rip them at the highest possible quality, and listen to them at the highest possible quality.

Sorry for venting. I just can't believe this thing sounds so bad. I've been testing a reading on-line all evening, and I am so disappointed.

All I need is to somehow test how the Zune integrates with the Alpine iDA-x100 which I am going to install in my car. If it does well (as I hope, since it is MTP compatible), I'll move to Zune in a second.

Quoting a CNN review (here: http://www.cnn.com/2008/TECH/ptech/10/06/review.zune/)

Now, this, like most review,may be somewhat biased. But they don't really sound they want to necessarily speak in favor of Zune.

If I wasn't laughing inside myself, I'd cry. For one time in my life when I bought something trusting the wide market success and random opinions, rather than gather data and facts, I am paying it as I deserve. I am such a Lemming.