I personally believe that the Zune Software is FAR superior to itunes. I wish that Microsoft came into the digital player game sooner than 2006 when apple already cemented in their status as the one and only standard of digital mp3 players. If Microsoft released a better product sooner and better than the ipod and ACTUALLY did proper marketing for it, we would be living in a different world revolving around a different brand.
I owned the original Zune 30, a Zune 8 GB flash model, and the Zune HD. I never owned an iPod until I bought my Touch 1.5 years ago and sold all my Zune stuff. I'm so glad I did. I immediately found iTunes far superior to "the Zune software", which never even had a name. iTunes is far faster with my large collection. iTunes lets me customize the view with much more flexibility. iTunes can play gapless reliably. iTunes doesn't grovel the hard drive endlessly looking for new media, which I vastly prefer. iTunes doesn't change metadata in my files from time to time forcing unnecessary backups. Neat little subtle features fall out of iTunes' superior design that simply are not possible with the Zune software. iTunes didn't force Windows 7 libraries on me like the Zune software did, which was a huge problem as Media Center followed the same stupidity of forcing Windows 7 libraries on the user as its only source of files, only it had an endless library rebuilding bug which made the Music Library unusable. Even if you never used Music in Media Center, there would be endless disk activity due to the bug, and thus I had to remove all folders from the Music Library, which had the side effect of removing all content from the Zune software as well. Microsoft only relented on this for the Zune software after hundreds of people assailed them in the old Zune forum. Note that the ridiculous things (WMP/WMC and the Zune software) used the same rigid method of defining the file source, but they maintained totally separate databases and disk grovelers, and Microsoft thought that was OK. I could go on. I can't think of a single thing iTunes doesn't do better than the Zune software, at least as things existed 1.5 years ago. I can't imagine this has changed any.
With hindsight, the only reason ever to own a Zune was the Zune Pass, and the Zune pass was terrible. Content regularly went missing or simply wasn't available to begin with. Tracks 10 minutes in length or longer were almost all "Album Only", meaning you couldn't download them with your monthly allotment of "10 tracks to keep"; you'd have to buy the whole album. And most albums contain more than 10 tracks, so to download an entire album to keep with your 10 free downloads, you'd have to do it over multiple months. And some of the encodings were bad and wouldn't play gaplessly on any device or with any program. However, I could buy the CD, rip it, and it would play gaplessly everywhere, except of course with Microsoft software, which has never been reliable at gapless. I ended up replacing all my Zune Pass "tracks to keep" with my own rips.
Microsoft is complete and utter FAIL for music. I would say that for multimedia in general, as there is superior free software for everything except TV. Media Center remains the only real game in town for DVR, and this is literally true if you want to use CableCARD. Otherwise, for library-type browsing, I'm using iTunes and its Remote App for music and XBMC for non-TV video, while for launching files directly from Explorer, I'm using foobar2000 for music files and VLC for video files. I can play everything, and no shady "codec packs" that can cause problems in Media Center are required. I continue to use Media Center for TV only because there is no other choice.
I say all this as someone who used only Microsoft software for multimedia (WMP, WMC, and the Zune software) up until I got fed up with Zune 1.5 years ago and bought the iPod Touch. It was my good experience with iTunes and the first Apple equipment I'd owned since the early 90s that helped me get adventurous with other non-Microsoft multimedia software, like foobar2000, VLC, and XBMC. It's been a revelation.
As for the future, and ignoring the streaming capabilities of the noisy, huge, power-hungry, expensive Xbox 360, the only thing Microsoft has got going for it in multimedia is the Media Center DVR functionality. It's literally the only thing on any computer that can do CableCARD. And sadly, by all appearances, Media Center is a legacy product for Windows 8 and hasn't seen even any bug fixes for several years on Windows 7. The opportunity is ripe for some other large company to swoop down and pick up the slack in this area, and it doesn't have to be on Windows. And then I won't need Microsoft at all for any multimedia.