I'd get a 60 gb ipod and run
rockbox on it. I don't have one myself but it is supposed to play flac and have gapless playback. My local hifi magazine gave the ipod video very good revievs in terms of sound quality but it's your ears that is going to listen to it. They also recommended the AKG K 24 P headphones and a lot of people seem to like sennheiser's px 100 too.
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