Originally Posted by rgeorg
Am I missing something?
You're likely missing iTunes Match. That's a $25 per year service that makes all your music files automatically available across all your iDevices and traditional computers, keeping them synchronized. No manual transfer is ever necessary. It can't get simpler or more convenient than that, can it?
As to transferring other file types, I have never felt it was inconvenient in iOS. For watching movies, I use AVPlayerHD. That app allows you to transfer a movie file via WiFi using any ordinary web browser on the source computer.
For transferring all other file types, the Dropbox app has served me well. But countless other alternative file managers / file transfer managers for iOS exist. For example, I use Filer to handle ZIP files in iOS.