Even past all the marketing, the iPod is a good product. Well designed, well executed, and has a barrage of support behind it. It has average (30Gb) battery life for its segment, and I find that Apple's about spot-on with the battery life predictions. There are three camps; those who see it as how it's being marketed, those who see past the marketing for what it is, and those who see it as how it's being anti-marketed. Anti-marketed, as in those people who'd hate iPods no matter what.
The HD5 has a nice headphone-out sound, in a consumer sense, and I enjoy listening to it, but the iPod sounds more 'natural', and less processed to me. And the HD5 (using IEMs) doesn't work well for classical music-- a lot of hiss. Still, it's enjoyable to listen to, a nice, warm, round, fuzzy sound-- reminiscent of a CD player, to me.