Tim. Sound quality is a function of how you've set up the software to do the conversion. If you have it set up for maximum compression, you won't get great quality but you can fit lots of songs. I have an 80gb version so I max out on the file sizes and for me, sound quality is excellent. Maybe you should've spent more time getting familiar with your ipod first Tim.
All I know is that I've had 3 or 4 other MP3 players before -- phillips, creative, etc. When I finally got the iPod, I was thinking -- Damn, I should've got this in the very beginning. The software is top notch and the playback of video AND music is terrific. Mine is 2, maybe 3 years old now and when my phillips was long toast (literally burned up) my iPod is still running reliably day in/out. Again, you just got to make sure that when your CD's or whatever is converted, that it's set 160khz or higher. I set mine min of 192khz and often even higher (256khz or 384khz) to maximize sound quality. Of course if you are relying on downloaded music, compression might've been max'd out to facilitate easy file transfer so you get what you pay for (zero). Then there is clipping. IF you don't properly set up the software to properly apply an appropriate signal strength value, the inputted signal could be clipped if set too high which WILL RESULT IN TERRIBLE SOUND QUALITY. The digitally converted file does not respect the analog limitations of the audio signal. Finally, may I just say that we are talking boomboxes here and not high fidelity. The output capabilities of the iPod, when properly set up is far better than most boomboxes are capable of reproducing, insofar as clean sound.