I was planning on getting a Zune sometime next year, once they beefed up the software/firmware a bit, but to my surprise, Santa decided hook me up with one on Christmas morning! I guess those cookies and Jager I left for him paid off...

My first impression of the Zune and the companion software was very reminiscent of hooking up the 360 or more recently, the Wii for the first time. In that, that hardware seemed solid and full of potential, but the software was nowhere close. I believe that this is both a good and a bad thing. The good being that you now have a device which is capable of achieving a countless number of additional features, given its unique hardware features. Specifically the onboard wireless and the windows live integration. The bad being that this potentially great device is quite limited for the time being, and may not be up to the standards of the veteran Creative players or even the iPod. Which, unfortunately, has become common place in this 'beta' software age we now live in.
With that said, I think there are some specific things Microsoft will need to do to in order for the Zune to be successful. First, it needs to ride on the coat tails of the Xbox 360. Meaning that it should have wirelessly integrated with my 360 out of the box...giving all 6+ million 360 owners an immediate need to ditch their iPod and pick up a Zune. Second, clean up the DRM mess. Do i use Urge or Zune marketplace? Why doesn't my Zune work with Windows Media Player 11? What do i do with my PlaysForSure tracks? Will it DRM uninfected tracks share via wireless? Finally, get me the features that will bring the Zune up to par and eventually set it apart. We need podcasting support, games, and a video marketplace just to catch up to the competition...and real wireless functionality with tighter live integration to surpass it.
So, buy one or not? Well, for me, the potential and the quality of existing features was enough...but i'm not conviced that its ready for the masses just yet. Afterall, its the hardware that sells it, and the software that keeps it.