Considering Ubuntu for son's computer

[episodic]

Will the latest version of ubuntu work fine with a 5g ipod nano?

 

[sivart]

Huh? You want to install Ubuntu on an iPod? Or are you asking if you can connect / sync an iPod.

If the latter, this might help:
https://help.ubuntu.com/community/PortableDevices/iPod

 

[Jovec]

From that article, no it won't work. However from here it says it will: https://help.ubuntu.com/community/iPodVideo

Your best bet is to try a Live CD/VM/test install and test it out before you commit. Or find someone with direct knowledge.

Recent Ipods - maybe 3 years old and newer - store the song info in an encrypted hash in an attempt to prevent syncing with anything except iTunes. I know there are/were projects to reverse engineer this, but I don't know how successful they are.

 

[JJChicken]

Would iTunes under Wine work?

 

[lxskllr]

Would iTunes under Wine work?

Looks iffy. Probably depends on the exact configuration...

http://www.jonathanmoeller.com/screed/?p=1647

 

[PCTC2]

Would iTunes under Wine work?

I've never gotten it to work properly. There's 3rd-party sync utilities here and there, but there's nothing that beats the native support of Windows and Mac OS X.