I like your post Danneq. IT's a good read and provides some useful information.
Thanks for relating your post with mine. As with most things on Head-Fi, you can get anything you want if you have the right budget. Budget can control a lot of factors. The Colorfly C3 honestly seems like a nice player to me and based on Colorfly's history, I'm not surprised by the reviews. I may honestly still pick one up just to have and through around for those times I dont wanna use my Tera Player somewhere. Also good to have options. I really like the looks of the C3 and at that price I can afford to take a hit on it if I decide to resell it. But that's just how I am. If I want something and it shows signs of being what I could find useful, I dont really care about price, I'll find a way to get it. Thats how the Tera Player came into my life
Older DAP's definitely have these issues with compatibility. I am not sure how the Zune works, but many people really like it's sound quality. The internal amp in the Zune is apparently much better than that in the iPod. I just don't know about the system you have to use to get the music loaded.
If you are ever trying to find out more about any of these devices, you should try using the "Head Gear" Section at the top of the forums, you should find most DAPs listed there and who owns them. Most Head-Fier's are happy to share their experiences, they just may not know about this specific thread.
If you can afford to get the Sansa Clip+ or Clip Zip (same internals basically) and another device later on, I highly recommend owning the Sansa player for the in between time. It's tiny enough you can get a FiiO E6 amp and have enough juice for most things if it even needs more juice to power whatever you are using to listen. It's not a very powerful player, but it's a pretty solid DAP, one you'll be happy to have to just use when you need it, even after you get something else. And at that price point, it won't set your other DAP ambitions far back at all. Also, many players use microSD cards and SD cards, so having a reason to stockpile microSD cards may help you when you get something more high-end, if you decide to get something after the Clip Zip (or Clip+).
EDIT: And don't forget, the classified's section of this website is a great resource for getting things cheap and in good condition. I always check the for sale boards even though I'm not really in the market for anything.
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As kenman345 writes, it depends on your budget. You can find newer so called audiophile players for $600-700, or you can buy a Sansa Clip+ for $50. Or something inbetween.
If you want to go for an audophile DAP, the best bet would be to try the Colorfly C3. If you want to try something older, you just need some patience in case you don't have access to a computer with Windows XP. If you don't need the same functions as newer mainstream DAP's, I'm sure that you will be happy with an older DAP.
Sorry if I did not help you with my post, but it is difficult to answer the question "Best audio quality portable music player". Most of them sound very good and there's most often not much difference. Buying better headphones will most often make most difference.