iTunes on my Mac shows that I have Downloads available, but won't let me download them. iTunes on the iPad lets me download said downloads, but I also run into the Downloading Error/Tap Arrow to Try Again. Repeat ad infinitum.
All times, guess what? I've been charged. Call them. They credit my account. Rinse and repeat.
Mac OS X SL 10.6.6 + iPad1 iOS 4.3, attempting to rent 127 hours. In most instances, the download actually gets to the end (1.3GB of 1.3GB downloaded), but then errors out. So it might be some sort of authorization error?
This was made even more frustrating when I was attempting to download this film while on vacation in Lake Tahoe. Download completed, but it never appeared on my iPad. Thus, I wasn't able to download it on my Mac (which was at home), then sync it to my iPad. This iTunes+iOS-device physical tethering is getting pathetic.
Looks like I have to surrender to the fact that I will never be able to rent a movie directly from the iPad, essentially defeating its go-anywhere spirit.