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I'd love if apple brought out a 500gb classic. Don't know if it's physically possible but my 160gb classic is full and I just HATE changing music around all the time, I'd love to have my whole library on me at all times, guess they'll never do it though.
500 GB would be nice. My mp3 collection of favorites barely fits on my 120 GB (LAME V0)...and a few dozen lossless reference tracks. Do like Bigshot does (I think that's his member name) and collect a few iPods...one for each genre.
Re the gapless on the Classic, I haven't thought about that much since I like to listen in shuffle mode mostly within a playlist. I do like crossfeed and crossfade though...one of my favorite things that Rockbox gave me with a 5G iPod...and it's so tweakable too.
Tonight I'm ordering a 16 GB 6G Nano...after thinking about it for 2 weeks. Orange, in honor of my dead (Orange) shuffle. RIP.