My kids love my iPod Touch. Twin #2 especially loves YouTube, where I let her download kid-friendly clips. Last night we went out to eat, and the order took a long time. She wanted YouTube, but the restaurant didn’t have WiFi.
Solution, I thought: download a movie from iTunes and sync it to the iPod in case this happens again.
First problem: the movies on iTunes are as expensive or more expensive than DVDs. Disney movies were running at $14.99 and $19.99 for high-def. That was a bit excessive, so I looked for the Dora series and downloaded and episode for $1.99. Cool, I thought.
Except, the second problem: Even though I bought and downloaded the episode, it wouldn’t sync to the iPod. I got an error that I wasn’t authorized to play it on the machine. I wanted it on the iPod, so I went through iTunes on the iPod and downloaded it there. It made me pay for it again, which isn’t cool. Songs can be downloaded by up to 5 machines without paying again.
Playing around some more, I found that even though I had bought and downloaded the movie with my iTunes account, when I played the movie on my laptop, it asked for my userid and password again. Now, I’m authorized to view it, which probably means it would have synced to my iPod without a second purchase.
I downloaded it with my iTunes account. I should have been authorized. Crazy. Any time I’m not authorized, a password prompt needs to pop up so that I can be authorized.
Lesson learned, I suppose. Good thing it wasn’t a $15 movie.
iggyantiochus on 
Dan
I hate iTunes. H A T E. I don’t find it intuitive to use, at all. I find it clunky and awkward, and ugly, too.
Does absolutely nothing to convince me that Apple products are superior, which is what the ‘cool kids’ seem to think.