WARNING: The following is a rant that loosely (at best) relates to the rest of the thread.
The only thing that would really surprise me in portable audio now would be the incorporation of Blue Tooth technology between MP3 players and devices like cell phones, PDAs, car stereos and computers. I've been reading that Blue Tooth has not been used as often as of late, that the technology promised too much too fast and is now fizzling out. But really, imagine being able to just carry your MP3 player into your car, and not have to physically connect it to your car, but be able to stream your portable audio digitally over your car speakers, and control it with your head unit. Or to be able to choose your ring tone for your phone based on one of the songs in your massive playlist just sitting two pockets over? Or what of storing data from your PDA on the large hard drives available now in many portable MP3 players?
Flac support would be nice to see, though it is not as important to me as seeing the amazing technology of Blue Tooth being integrated between different consumer devices. What's stopping them, especially Microsoft?