Tom,

Regarding your Squeezebox not doing play lists..
Because the whole Squeeze thing is open source, there are tons of free add ons to do pretty much whatever you need to do with playlists. "Moose" is a popular one. I personally didn't find the interface appealing but it did do everything I needed, including allowing me to build long or short play lists or create ones by mixes of genres and still play random. I like random for some reason. Anarchy rulez!! \:D
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With great power comes Awesome irresponsibility.