No.
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Music-wise, jailbreaking does not get you any free music that you wouldnt have had without jailbreaking it. You can find free music anywhere online, with or without a jailbreak. Jailbreaking does not get you free music, but does get you mods, apps, etc.
Yes, iTunes store. It comes with the iPod.
Rip the music files to your computer and then sync the ipod to it via itunes
, As an iPod Touch user, I have found out how to download-and-play songs on-air without the use of iTunes. Apple has not yet released such a function, and the program is not approved by Apple Inc. The requirements to run such a program is to "jailbreak" (hack) your iPod Operating System with specific programs around the web, and through software which exists on your iPod right after the jailbreak, you download the program. For both copyright and legal issues, I cannot write down neither the jailbreak method, nor the program to download the songs. The only thing that i can do, is to redirect you to www.ipodtouchfans.com . Hope this helped.
The ipod nano without the video and the ipod nano with video.