How do you transfer iPod songs to your library that thinks it already exists on iTunes?

For christmas, it's hard to choose what to add the christmas gift listing, iPod nano 4th or zen x-fi?
Besides, it can put tv shows on ipod and play ipod on tv, the most important, without apple tv, that's really great, may be I should get iPod.
But friend said, I need DVD to iPod converter?
Does it like dvd rippering software can rip DVD to any video format ??

I have a headset w/ mic I used for making Skype calls on my computer, can I use that same headset for making Skype calls on my PSP or do I need to buy a specific type?

I just convert DVD to p3 with ps3 dvd converter but not run skype on ps3, yet.