I agree, the next generation of portables should take the empeg "car/home" design to the next level: "portable/car/home." We've talked about this before, but I'll rattle it off again for no good reason.

The new generation should be a portable should be hard drive based with a nice screen and good software. Also, it should be able to insert into its specific single DIN car deck. The car deck will have all the front panel controls and a nice screen. Lastly, the portable should have a home dock which, like hybrid8 said, should be more than a connection to the PC. A standalone box with a screen (as an option) would be nice. It would be even more nice if the home box had RioCentral (I think) ability to feed sound streams to other boxes in other rooms of the house.

21st century, connectivity, portability, simplicity, and freedom to have ALL of your "stuff" wherever you are.