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Ok upon further dicking around, I think the main problem is WMP seems to be having massive issues with the mp3 tag information. Renaming, or using the "Advanced (pfff!) Tag Editor" locks it up for sure. Everything else seems to be working okay at this point.

I think we're going to be going with iTunes on this machine.

I love my music organizer. I call it "folders" I just like having total control over the structure of my files. I've used iTunes and Picasa, but I didn't like the disconnect between the program and how the files were physically stored. I feel like I'm losing track of them. I may start using iTunes again, since you can set it up to not take control of your files.