My library is stored in FLAC. Pre-squeezebox, I would copy a chunk of it
at a time to mp3, import into itunes, and put it on my iphone. In
itunes, I use smart playlists pretty extensively, mostly parsing out
into genres, and refining by some combination of play count, last
played, and rating.

That worked great for playlist management when I used my iphone for all
listening. But it was bad because i used my iphone for all listening :).
Now that I've got a SBT ready to go, one of the first things I'll want
to try is getting my smart playlists "converted" into squeezebox
playlists, and that should be fairly standard with erland's plugins. 

What I doubt I can do is to set things up in a way that merges SBT
activity with iphone activity. I think that I will still need to have
mp3 versions even if I eliminate itunes and stream my libary over a
cellular network...my understanding is that you can't stream FLACs
unless on wifi. For some stats and playlists, I would like to set up
something where song.flac = song.mp3. In other words, if I have a
playlist of unplayed songs, whether I play it at home via the SBT (FLAC)
or via iphone in the car (mp3), I would want that song removed from
unplayed both places.


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