Not being a big Apple user (the iPod is it), I wasn't very familiar with Apple's MO.
I was watching the Screen Savers on TechTV and they said that the early adopters will pay the $299 and then Apple will drop the price to $249. My long-time Apple-using friend said the same.
However, even at $249 I think it is overpriced. The other factor is that if this is a "sports player" for people on the go, is having a platter that spins quickly in it a good idea? I'd prefer a flash-based player for my infrequent gym visits.
My long-time Apple-using friend's opinion differs - he quite rightly points out that flash players have a much smaller song capacity and he doesn't want to download new songs everytime he works out.
My counter to that though is that flash prices drop rapidly. The 1GB CF card i bought for my digital camera last year cost me the same as the 128MB card I bought a few years before.