Mid priced ($100 - $500) - Offerings from Fiio or iBasso
High priced ($500 - $2000) - Offerings from Hifiman or Astel & Kern
These are probably the 4 major players in portable players, but certainly not the only 4. For research purposes, I'd suggest you head over to head-fi.org and check out their portable players forum.
Whatever you do, don't go over to head-fi.org. You are likely to be sucked into a time sink of 1Tb SSD modifications to your 160Gb iPod. Seriously, I almost bought the pieces right then and there, even though I have a perfectly fine 160Gb iPod. When the drive goes, then I will take the plunge.
I agree. There are some serious listeners over at head-fi. They'll think nothing of spending several $k on a "portable" listening system. I ventured over there on advice for my first set of good cans and amp. Feel lucky to only have spent $500.
The iPod classic is what I use in my car audio system and I need a new one. I hadn't realized they discontinued them until now. If anyone has one for sale at a fair price let me know.
Still love the original ipod Video...I just keep replacing the batteries.
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