I got an e-mail back from support tonight. They set me up to re-download all of my purchased content (500+ items!). 🙂 That’s better than I needed…I really only needed the items from the past 3-6 months.
iTunes is going nuts downloading things right now. But, for the record, I didn’t really have to raise a fuss at all besides the e-mail. They apologized and said that the ipod->PC sync up is a relatively new feature, and that they are planning to enhance it in the next release to make sure that the user has authorized before iTunes begins the sync. They also asked me a few questions about the scenario that I encountered so they could try to reproduce it on their side, but they set up the re-download before they asked any questions…point being, they didn’t make me jump through hoops.
So, in short, iTunes continues to be awesome. 🙂