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I went through a painful iTunes experience. Had to. I try to avoid iTunes as much as possible, but since I wanted to update iOS version on my iPad, it was not possible to avoid it. The bottom line is that it sucks as a device management tool. Here's why: iTunes is not a device management tool It is a media management tool. It was made to put music and videos to iPod which started as an MP3 player. Some say it sucks there as well. I don't care. I copy photos as files, I transfer music with MediaMonkey and use mail and Dropbox to manage documents. iTunes is patched to be a device management tool with key functions obscured by the media-optimized interface. Sync doesn't One of the most scary checkboxes in the Apple universe is the " Sync Apps ". User is warned that if selected, all apps installed by the user on device will be removed. And they are. The trick is that before one does that, it makes sense to " transfer purchases ". So that after ...