[mdodge]

Like the others said it is a little tough to compare different classes of devices. However, if you talking straight music playback quality comparison there are a few things to consider. The IPOD of course is designed mostly for music but therein lies its drawback. The TP can do it all. And I know its not just me, but being somewhat of an audiophile, I can't stand any of the IPOD's out of the box sound quality. Throw in the fact that there isn't a custom EQ and it makes it worse. Sure the inteface is easier to use and the battery will last much longer than useing a smartphone.

But with a winmo device, you aren't stuck with the same level of quality. By that I mean all of the different players available for winmo (with custom eq's) and in some cases the ability to use better sound drivers. Case in point, you can install the WOW HD drivers on the touch pro which increases fidelity a good amount.

A good pair of headphones is always key if you concerned with quality. If you really serious about mobile audiophile quality then you will get a headphone amp as well. But comparing the 2, you will ultimately get more use and better sound from a TP than an IPOD if you willing to deal with customizing, worse battery, any possibly a worse interface. Since I want sound quality above all else, I can deal with these. And storage isn't to much an issue since I have a 16GB microsd card to hold my music. I now barely use my IPOD only for my car, which is still easier to use while driving, but considering the EQ's, amps, and high quality speakers I'm outputting to, I can make up for the IPOD's lack of sound quality. Plus with an IPOD you cant play flac or other good lossless audio like I can with a good player on my TP (coreplayer)

Here I'm really only comparing straight music playback of the two. Other feature considerations may apply.