I certainly see how the combination of Pandora and Simplify Media would keep someone very happy musically.
Of course, it requires ubiquitous broadband. The 3G is one of the few devices coming anywhere close to providing that, so, in theory, that side of the equation is solved.
But don't throw out your empeg right away, though. See if this idea of your works first. I think there's a good chance it might fail on a few points:
First, even with the existence of Simplify Media, I'm not convinced it's got the same useful feature set for on-the-road browsing and searching my music collection that the Empeg has. Hierarchical playlists? Arbitrary playlist groupings? Ignore as child? Alphanumeric searches on a tactile remote? Those things might not be important to you, but I know they're critical for me, and for a lot of empeg users.
Second, 3G reception patterns. Can I take a drive from Seattle to Portland without a hiccup in the music stream? What if I drive through a tunnel? Or better yet, what about a trip from Seattle to Vancouver BC? Have you *seen* how much Rogers charges for data traffic?! I don't recall where you live, and I don't know where you travel, so maybe that might not be an issue for you.
Third, AT&T's *supposedly* unlimited data plan. I've heard rumors of people with the *original* iPhone getting cut off because of over-usage of their data channel. Imagine what will happen if they notice a 3G user streaming constantly. Betcha we see some people complaining about bandwidth throttling on their 3G iPhones soon.