Spending a little time getting to know iTunes and setting it up properly will save hours of frustration and band-aiding later. I have my iTunes set up and running and syncing between my iPhone, iPad, 2 Mac's and a Win7 machine. Yes, I spent time getting everything set up (nearly an entire afternoon) but now, I can easily transfer music, shows, apps, movies between all the devices so easily it isnt even funny. AND, I can use any of the 3 PCs to add movies, music, shows into my library and it all sits on a NAS disk on my network. I even connect my 2 Apple TVs to it for movies, music and shows all the time. I have over 1000 episodes of shows, 500 movies and upwards of 2500 albums, so it is working just fine.
Say what you want about iTunes, but once set up, it runs great. Learn it, you will love it. Runs so much better than my old Media Center 2005 PC ever did.