The Zune software turned out not to be so great at working with iTunes playlists. It’s not a dynamic synchronization, just a one-time thing. So after asking the Zune to read my iTunes playlists, it did so, but after I changed my playlists in iTunes, the Zune did not see the change. Also, the Zune does not attempt to pull in the smart playlists, just the static ones. Even just treating the smart playlists as regular ones and pulling in their current contents would have been great, but no.
My last gripe is that there are playlists I can’t get rid of with the attractive names “__127.0.0.1” and similar. Why is the software showing me its disgusting internal details?
The possibly good news is that Microsoft have just done a major overhaul to the Zune software, and so some of these problems may be gone. On the other hand, they may be replaced with more ridiculous problems!