Trouble Manually Managing iPod

After upgrade to Leopard from Tiger, trying to manually manage iPod 30GB. I have tried either "sync only checked songs" "Manually manage" or both, but unchecked items remain on iPod. Also, I am trying to sync my wife's 1GB Shuffle either in her account with Shared music or in my account with a separate library. Songs I put in my Drop Box do not appear in iTunes under her account or in her Drop Box. When I use my account but a new library, I add music to her Library from mine, but songs will only go to Shuffle when I check Autofill.
I am open to suggestions.
Thanks!

After searching through more help files, I tried a few more things; 30GB: checked Sync only checked songs & Manually Manage. Shuffle: Manually Manage was not a choice, but the help file instructed me to drag the songs we wanted from the library to the Shuffle.
I hope I can recreate what I did, because these steps seemed to work.

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