1 mac 2 users, 2 iphones(+), 2 itunes libraries and 1 itunes account!

Hi.  This is an enigma!  Both my husband nad I have iphones which we sync with my mac although on different user accounts.  We both use different libraries but also both use only 1 itunes account. 
Problems 1:  Husband has created his own account now but how do we transfer the purchases he has made via my account to his?
Problem   2:   We both have found since upgrading iphone that we have duplicae enries all over the itune on the iphones only - not showing up in the individual iTunes libraries on Mac.
We have not had any problems for a long time with syncing - not since this new software.  I have my account enabled on my iphone for game centre etc, but my husband has closed his as he keeps getting my details flashing up. 
Not sure if this is an itunes issue or iphone?  Both I think!
I realise that until the 'accounts' issue is sorted neither of us can use iCloud which is extremely frustrating - speicially as I just paid and downloaded Lion!
SM

I vaguely recall reading about some commercial library manager that is supposed to help with merging libraries.  Simply adding the files will not, of course, carry across playlists or some metadata some people want to keep  such as playcount, ratings, last played date, etc.  However, all the ways I can think of doing that are pretty complicated (and the commercial utility basically uses some of those tricks).  You may be able to do playlists by exporting them from one library and importing in the keeper library.

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