5000 Crashes In Your Pocket
Microsoft has proven time and time again that they are clueless about design. It's just not part of their DNA. Their corporate environment does not cultivate good design and does not reward good design. Just look at Windows Pocket PCs and Windows Mobile Smartphones... all very awkward to use!
As we are all aware, Microsoft likes to try to enter markets, which others have created, by copying others' products. But, they always seem to have a hard time grasping the essence of what makes the original product so great. And their copy usually misses the mark. I'll really be surprised if things are different this time.
Add to that, Microsoft typically has a difficult time getting the software technology right on their first several releases of a new product. It makes you wonder who they have coding these things... newly hired college graduates who are still learning from their first mistakes? So, if history is an indicator, I'd expect this product to crash and hang a lot and not to have good battery life (due to the bad software architecture decisions that Microsoft tends to make in rev 1 products).
In any event, even if Microsoft does get this product mostly right, I doubt that it even matters now. The game is over. The iPod has won. It does not do any good to bring in your star relief pitcher after the final out of the ninth inning.