i know you said you don't want in-ear phones, but have you tried them? I was a bit dubious myself about them at first, but I've become a total convert. And the e2c's are right in your price range. Get them from headphone.com and return them if they don't meet your needs. They're very nice, and their only drawback is also their greatest asset: the isolation from the outside world, which can be good or bad depending on your needs. Personally, I like my ER-4P better, but they're more than twice the price.
I find the output of my 10 gig 3G ipod to be somewhat lifeless with significant roll-off at both ends of the audio spectrum- even with non-compressed AIFF's from iTunes via my iBook. Unfortunately, my trip back to the Apple Store (to rule out a defect in my unit) found all 3G iPods sound similar to me. As many have noted, Apple's buds are suboptimal. My iPod still sounds dull with KSC-35's, Senn HD280's and even Grado SR-80's.
Then I dusted off my V-6's (moded with those comfy Beyer velour earpads). Success! Acoustic Synergy!!!! This efficient but notoriously bright headphone actually sounds decent with my dull iPod. Now I need to find some earphones to match.
I love the iPod's ergonomic design, I just wish the sound quality matched the unit's exterior beauty. I may try some Sony EX71's or Shure's.
you mentioned a preference for non canal phones but said you were open to suggetion; I definately like my Etymotic Er-6's unamped with my 3rd gen 15gen ipod playing self encoded Lame VBR files.
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