Okay, so I’ve had the Zune for a while now. Here’s some more thoughts:

• The official 1.2 version is out, supporting Vista fully. I probably shouldn’t have hacked together an installation earlier, because installing the official 1.2 version just forced me to re-do my library. Oh well, my dumb fault. Other than that, smooth sailing on the upgrade.
• There’s no way to easily define what “type” of video you’re putting on the Zune. For example, in iTunes, you could right click on a video and specify that it’s a  TV show, or a music video, or movie, etc… but not so in the Zune software, at least not yet. Microsoft has an overly-technical writeup on the Zune site on how to provide content for the Zune with the proper metadata, but this won’t be helpful to consumers at all; just those mass-producing content for the Zune. Here’s hoping a newer version fixes this problem. Also, please, let us mass-set this categorization across numerous files! In iTunes, you couldn’t just select a bunch of videos and set them all as music videos.. you had to go through them one-by-one. Ugh.
• Microsoft is fully onboard with the Zune, it seems. This is good news, and hopefully they stick to it, to keep a strong competition going with Apple.
• The software reminds me too much of Windows Media Player. It obviously was based on the WMP codebase, but there’s just some design decisions I really disagree with, such as the sidebar to the right that tries to contain a playlist editor, sync list, burn list, and “what’s playing” functionality, swapable by clicking icons above the sidebar. I just hate that sidebar, and almost always want it closed.
• Playlists do not remember what order you sort them in! This was a feature in iTunes that I used all the time, and really miss it on my Zune. In iTunes, it would remember specific sorting rules for each playlist, even smart playlists. It would also transfer this sorting to your iPod. I found a way to sort of hack-it in the Zune interface, by using the sidebar’s playlist editor, and forcing it to sort by album, etc. — but that has problems of it’s own, leading me to my next point:
• When you choose to order by “album” in the interface, you get a smart sort based on album, then track number. Good. But if you do this while making an auto playlist, like so:
  
  You do not get this smart sorting method. You instead get an album title sort, with no secondary sorts thrown in. Your tracknumbers are random, but your albums are clumped together. Huh?
• The Zune marketplace has about the same timeout problems as the iTunes store. You may double click a song to preview it, and a few seconds later get a time out message. Really annoying. Also happens if you’re downloading/buying content from the Marketplace.
• The protected Zune marketplace files are sometimes too “picky” about being re-synched to a Zune. The rules may be different for non-ZunePass files, but on mine, after 3 syncs (add it to the Zune, then remove it, etc.) to the Zune, the file will no longer transfer, and you have to re-download it. I ran into this a lot, when I first reset my Zune and re-added all of the songs… most people probably won’t run into this problem, though.
• There’s no way to select files in an auto-playlist and be able to delete them from the hard drive. If you select files when just looking at a normal playlist, or your “library” view, you can select any number of files, right click and select “delete”. You get asked if you just want to remove the files from your library, or if you want them removed from your library and hard drive as well. It would be nice to be able to do this directly from an auto-playlist. I believe I could, in iTunes.

More bulletpoints to follow as I find them. I still stick with my decision to go with the Zune, and haven’t run into any dealbreakers for me yet. Don’t take my criticism as negative press! Just small complaints.