The iPod is designed specifically to prevent this type of filesharing. There may be cracks available but I can't point you in that direction because it would be against the law and probably also against vDr policy.

The easiest legal way to do it is to copy the files from iTunes to a CD, then import the CD into the next iTunes library and upload the music to iPod #2. Sorry it has to be so complicated! If you don't like it, write your senator and tell him/her to repeal the DMCA!