Squeezebox Server (SBS) can read playlists in the standard m3u format. I think iTunes can export playlists in that format, but I'm not sure because I haven't used iTunes in a long time. I mostly use MusicIP for making playlists -- it works like iTunes' "Genius" and integrates very well with SBS, although setting it up can be difficult. But any program that can save m3u format playslists will do, and there are many of them, so pick one you like. Other examples are Windows Media Player (which I can't stand), foobar2000, winamp.
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