Strangely enough, my iPod has no problem whatsoever downloading and playing songs purchased from iTunes. (Relax Ryan, I only got two. Make that five. Whatever) Which leads me to believe that
notaboxer is right and there is something wonky with my computer. Which, considering it's origins, is not too far-fetched. It's just an old, should be dead server after all.
I'm thinking I need a bigger purse. Cell phone, day runner, iPod, little journal, pen, lip gloss and keys are a tight squeeze in my current one. Unless of course I fully utilize my little fruity buddy's functionality and start using the calender and contacts. But that would make sense.
Edited to add - I feel like one of those people in the orginal iPod commercials, dancing around with the buds in. I'm totally falling in love with this thing.