Yeah, turns out iTunes doesn’t like symlinks. So having some folders in my iTunes library symlinked to another drive worked as long as I wasn’t adding new files into that folder (like podcasts). Podcasts would never leave the download directory and get moved into the symlinked root.
So I just got a bigger drive, which is not what we would call a “scalable” solution. I’m at 500GB now, and with me adding more and more video into my library, that isn’t going to last too long.
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