Help with two Ipods on Same Computer

I have several questions in this one thread...
I have two Ipods (Mine and my wifes). We each have seperate user names on the PC. I have all my music in the Public Folder, Music, Itunes. I have both Itunes preferences setup to share libraries, I have both setup to use that as one library, and I have considated the libraries. So the problems:
1. How can I insert a new CD we own and have it be in the library and both Ipods sync it? I placed a new CD we own and it is syncing to my ipod, but not my wifes. I confirmed it is in the shared folder.
2. Can you both use the songs you purchase on Itunes? It is saying no when I am syncing hers for songs I purchased on my acct. But I thought it could be on 5 different devices.
Thank you for any help. I have searched high and low and I am sure the solution is here somewhere, but I keep doing what I find with no success.

If the old iPod works, the new iPod will work.
Simply plug it in.
Create a new playlisy with the songs you want.
Open iTunes orefs -> iPOd.
Select Automatically update only selected playlists.
Select the playlist you just created.
That is all.

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