Yah, I certainly don't do any media consumption. I have a mac mini as an itunes server, feeding 3 appletvs and 2 airport expresses, plus ipads and iphones and ipod touches, many of which get used simultaneously. With 4 kids, we can have as many as 6 different streams going on simultaneously, all without issue. I've got ~700 movies on the server, many thousand albums, ~50 tv series all on the server. Of course, I also have the media for all of those, so I was able to rip them into a format apple supports. When someone else rips what you're watching, I can see how apple might frustrate you when it comes to media consumption.
There's a reason I'm an "apple fanboy". I've been working with computers since 1982. I've worked with effectively every platform, both personally and professionally. I admit I haven't used a version of Windows since XP, so it's possible that there have been huge advances since then, but at this point, I'm not going to replace everything I own. I switched because it worked better. From the bsd underpinings to the superior data management, I haven't worked with anything that from a user's perspective works better. All the power of the unix command line and a graphical user interface that actually works logically and consistently. Instead of relying on flat files, iTunes uses a database infrastructure that allows tremendous flexibility for interacting with your media. Sure, you can't just drop files in a filesystem and have them be available, you actually have to load them into the database. Which CAN easily be automated.
But further to suggest that Zune is a solution, especially given that even microsoft feels like that was a failed experiment, is ludicrous in the extreme. There may be a lot of different solutions to the media consumption problem, but Zune certainly isn't one of them.