Syncing music on 2 different iPods/music libraries w/o importing the CDs twice ?

Question

Hello to you all support community,
     Here's the thing : my brother and I bought together the full 2009 Beatles remaster box with their complete recordings and all.
     We both have an iPod and separate iTunes libraries on separate accounts on the same Mac. Here's the really stupid thing : if we both want to have the 2009 Beatles remaster on our iPods we need to have it on both libraries on both accounts, thus we need to import the CDs twice, once on each account, once for each iTunes library !
     That makes no sense : the data (a few gigabytes worth of music) will be written twice on the very same hard drive, where we only bought the music once, for the both of us. Sharing libraries does not fix that at all as it does not enable cross-syncing of parts of our music. And we don't want to share an iTunes library because we don't have all of our music in common, nor do we want to share an account for similar reasons.
     What is there to be done ? Is it a matter of author rights violation ? That won't change anyways, because the result is the same : the music from CD or set of CDs is synced twice on two different iPods, wether we import it twice on two different libraries or find a way to share the music and then import it just once. Thanks for helping !

Answer 1

No, not on this computer as i only copy the music i want from this library to my iPod.
Yes i am managing it manually by copying it myself and now i wanted to switch to syncing the music only.
The Sync Apps is currently checked but when i try to uncheck it it said to remove all my apps from the iPod.