Sharing iTunes Library between Snow Leopard and Windows 8

My setup:
2006 Macbook, running Snow Leopard
Microsoft Surface Pro, running Windows 8 Pro
Toshiba 1TB portable external HDD
I am using my external HDD to host all of my media content, including my iTunes library. When I want to take advantage of the portability of my Surface Pro, I connect my external HDD to my MacBook, and use my MacBook as a media server. When it is connected this way, all of my music is in my iTunes Library. When I use my MacBook to listen to my iTunes library, all of my music is there. The problem is when I connect my external HDD directly to my Surface Pro, some of my music is missing. This is inconvenient because it leaves me without the ability to add new music or delete music from my iTunes library unless I am working on my MacBook. I have already tried ripping my iPod, which actually has ALL of my music on it, and transferring it directly to my external HDD. When it is connected to my MacBook directly, it looks like that actually worked. However, if I connect it to my Surface Pro or use my MacBook as a server and connect to my external as a network drive, the music is missing. Am I missing something obvious? Has anyone else had this problem?

Sounds like some of your music on external drive is in file format that Windows can't read. Am I missing something?

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