Two different apple ID's with purchased songs in one library

I have a user who had an ipod. Had several disks and 100 songs or so purchsed under email lets say [email protected], He then purchased an iphone and setup the phone under [email protected] on his work computer. He wanted his music on his work pc so I copied his files from that machine to a portable HDD. Copied the data back to the work PC under the ipod music directory. Selected add folder to library and thye showed up. It asked him for the login for that apple ID and all seemed to work. Just recently it keeps asking for the login and then pops up with the old ipod account as the name. We eneter the verified working password but nothing happens. it just asks again. Those files are sync to the iphone and play from the phone but do not play from itunes. I think the current I tunes version is from an update about 2-3 weeks back, so semi current. The iphone is a 3g and on the latest software. Any known issues with this ability being disabled or suggestions?
Thanks,
Brian

Thank You,
The majority of the songs are playable. I think these were all imported / purchased on the newest account which works fine. It appears he purchased music from 3 different accounts. The newest and some with [email protected] and others with [email protected] When I go to retrieve the password from the apple site it says the other two do not exist. These email accounts are long gone as well. I also tried entering the other two addresses under the field that is given for old accounts. Any ideas on who I can call to see what that password is still available from Apple. If not those songs which were purchased are worthless at this point. Well they do still play on the Iphone just not from Itunes which seems weird. What / who decides to close these old accounts with Apple?
Thanks,
Brian

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