I think that for the $35 that PortaPros cost, you really can't get much better sound. I think that at ANY price level, cans sound better than buds, but I have never spent $100 on buds. If I get into the real money area, I'll pick up some Sennheiser cans. A friend has some $450 Sennheisers and they're excellent.
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Work: the 8 hours that separates bike rides.