Adding songs to a new iPod Classic

I have an older 80GB Classic and I am easily able to manually add songs to the iPod by dragging them from Windows File Explorer to the Music portion of the iPod in the iTunes program.



My wife has a new 160GB iPod Classic and I'm trying to add songs to her iPod and am getting very frustrated. The drag and drop doesn't seem to be working. I tried to sync a small number of songs to see if the would work and it just synced some of the songs that are on my older iPod.



Here's what I want to do:

-I have file folder on my Windows computer with all of my songs.

-I have a different folder on my Windows computer with all of my wife's songs.

-I want to manually drag songs from my Windows folder to my iPod (that works)

-I want to manually drag songs from my wife's Windows folder to her iPod (that doesn't work)



I have iTunes 12.0.1.25

The software on my wife's iPod is 2.0.5

The software on my iPod is 1.0.3



In the iTunes summary page, I have the "Manually manage music and videos" checked. However, when I try to drag and drop a song to my wife's iPod, I get a red circle with a slash through it when dragged to iTunes. When I eject the iPod and close iTunes and reload both, "Manually manage music and videos" is no longer checked.



What am I doing wrong?????

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