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If i may:
go to anything but ipod dot com
and read the forums there. I am a long time poster there - AFAIK, there is no ebook reader that can do what you need done in terms of mp3 playlists [unless you look at Android tablets possibly but then you are cracking the 400USD barrier].
Quite frankly, to my ears and to my headphones, nothing beats a dedicated mp3 player/DAP/PMP in terms of sheer audio fidelity.
The Clip+ is an excellent player, probably ounce of ounce, the "best" sounding audio player around. And it is cheap as hell, is extremely durable and takes microSD cards for near limitless expansion of your library.
If you install the opensource replacement firmware called Rockbox on the Clip+ you will be able to have on-device playlist management.
The Clip+ is not the fanciest player out there and battery life is limited to around 12+ hours real world usage. But it is an excellent device to consider.
MODS: Apologies if the referral to another site is inappropriate. I will edit and remove and contact the OP via PM if necessary with the suggestion to the other site.
cheers,
-les
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