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I prefer emusic.com for DRM-free mp3s, and Amazon.com and iTunes also have some DRM-free music. Your Pocket PC should be able to play the unprotected AAC files from iTunes with TCPMP and the AAC plugin.
For downloading from Youtube, I use a Firefox plugin, but you can get an app to download straight to your Pocket PC. TCPMP will play the flv files with the FLV plugin.
m.youtube.com is also handy if it works on your device, it appears they have increased the amount of content on the mobile site recently.
I use TCPMP as well, but its not very handy for mp3s - I would prefer a more foobar-ish view of my music with the playlist displayed instead of the album art. I use pPod for playing mp3s along with Sony Ericsson's Disc2Phone software to convert my mp3s to 128k from whatever they are and put them in the proper folders. Oh, and I mostly use a proper mp3 player (Meizu M6 right now) because of the battery life, sound quality and features.
Whew. Long post, hope it helped.
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