Why would anybody expect this new player to be any different than any other m-s product? It all has a "I am smarter than you" attitude, and is never ever designed to work the way that I work and think. Never. So until somebody comes up with an aftermarket OS that can replace the arrogant and wildly-different-from-the-way-I-think functionality, my advice would be to avoid purchasing it unless it is sold really cheap with a double your money back if it does not play within an hour warranty. After all, a company that is willing to repeatedly sell products that are not finished engineering can't be expected to ever produce quality software, can it? Also, it would not be acceptable for a new car to need the engine re-installed before I could drive it home the first time.
Atrocious. But so expected. You said Microsoft, right?
The whole question is why didn't you just throw it away after 30 minutes? Why should anybody have to put up with such an arduous task just to get it "out of the box" for an experience? And from the king of s/w too!
The other question is "Why bother?" Zune. Yeah, right, keep dreaming MSFT. Either you're cool and you buy Apple, or you're an otherwise-normal person and go for just-as-good-but-lots-cheaper, sorry-no-white-earbuds. Did I mention cheaper? Sansa et al fit this bill, as you say.
But then I've bought the cheap almost-as-good stuff too and had the same start-up problems, but you kind of don't mind so much, after all it has a name you can't pronounce and a sheet of paper instructions in broken English.
Imagine if your new car couldn't make it off the car lot without 3 calls to Henry Ford and 5 runs thru the service bay. Sorry, you have to provide your own gas and oil before you drive away.