[ailurux]

I think this is an example of the Windows line ending bug, at least if those text files haven't somehow been converted along the way, because those do contain Windows line endings. The longer one I'm not sure why that would crash, but I did notice it has some .m4a tracks that won't work with Tangara so maybe related? I've made much longer playlists without issue so I doubt its to do with the size alone.