iPad Operating System and iTunes libraries consolidation

Two missions: First trying to consolidate multiple libraries within my family. Have iTunes on laptop (windows xp) with 55GB of music on it which is sync'ed with sons iPod and my iPod. Also have a iPad which my husband has bought a good amount of music on. Will I lose all of his purchases if I sync the iPad with my iTunes library? Should I burn CD's from his iPad (can you do this) then reimport them into my iTunes library??

Second mission: Because the iPad is older it needs a upgrade to the operating system and the only way I understand this can be done is through a sync with iTunes (newer versions allow this to be done on the iPad itself). It has never been connected to a computer.

THANKS Techie folks!!