I have my music stored (as FLAC) on a simple windows 2000 PC stuck to my
garage wall. I'm buying a laptop for the first time, and I'm stuck on a
Macbook. I'm also planning on buying a ipod as it now supports gapless
playback.

I want a mp3/aac version of my entire music library on the laptop
managed via itunes so that I can do the whole playlist/syncing to my
ipod. 

I know I can use foobar to convert my library to mp3 and copy it over
to the laptop (after a couple of days), but how to keep this
up-to-date?

Also I'd love it if my playlists created on the ipod could be used by
the squeezebox? I understand there is some integration between
Squeezeboxes and Itunes, but since my music is stored in FLAC I don't
know if that's an option. 

Anybody got any ideas on this slightly off-topic post. 

Thanks


-- 
sdevans
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