Hi, Nuly.You do not mention whether your computer is PC or Mac here.
This
iPod Transfer Software can transfer the files from ipod to computer, ipod to iTunes, ipod to ipod.
well , If you are a mac user.maybe you can try to use a professional software to meet your need and you can first have a free trial .
This
iPod to Mac Transfer is an excellent iPod and iPhone management tool is specially designed for Mac users. It can fast transfer, rip, copy and manage your music, videos, photos, podcasts and TV Shows between iPod/iPhone and Mac and add them to your local iTunes library.
For your second question, i think
DVD Video iPod Converter can help you.It can convert any dvd video on the market now to iPod MP4/H.264 video.