VERY bizarre problem, not sure of the forum, files becoming corrupt...

Alright, a day or two ago I started encountering something very strange in my iTunes library. About 6 years ago I made the jump from Windows to a Mac. Naturally, I brought my media library with me. I've had the same computer all these years, and a little over a year ago, migrated my iTunes library to a 1tb external drive. Since then, I went back to my CDs and re-encoded most of my music at a higher bitrate than what I kept it at on my Windows machine. Some of the music I didn't or couldn't re-encode. Same went with a few of my movies. Now, a few days ago, some of this low bit rate Windows encoded material has suddenly become corrupt for no reason that I can see. It appears normally in my library, but without any artwork. When I try to play it, it immediately plays the first song in my iTunes library. Trying to play the same file in other programs (Quicktime, VLC, Finder's preview, etc.) gives various error messages, all basically saying the file can't be read. More and more of the files I carried over from Windows come up with this problem every day. It's not a staggering majority of my library, but some of the stuff will be difficult to replace for various reasons. The only change I've made to my computer set up recently was adding an Apple TV onto my ethernet network.
Basically, my question is, is this any kind of a known issue, or is my disk going bad, and strangely the files that are going corrupt first are the ones I carried over from Windows? Should I be worried about my recently added files?
Any and all help is greatly appreciated.

The drive reports no errors of any kind. I also doubt this because, exactly like I said, it's only files carried over from Windows that are doing it.

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