iTunes Syncing Woes

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First off let me start by saying that I love my iMac, but Apples copyright protections for syncing and authorizing computers is absolutely horrible and next to impossible to use.

My fiance and I have our own apple ID's and purchased an iMac together. We have separate profiles on the computer. I set up itunes on my profile with no problems. I authorized the computer with my Apple ID and downloaded all of my previous purchases from the cloud...... absolutely no problems.

My fiance logs onto her profile, and starts up itunes and runs into all kind of problems..... some of which I managed to solve. At first it said that 5 devices where already authorized, so we de-authorized all of them and authorized the iMac with her Apple ID. That unfortunately is as far as we can get.

Here's the problems we're still having:
  1. iTunes won't let her sync with her ipad, unless she's willing to let the system wipe her ipad clean.
  2. When we tried to download her previous purchases from the cloud it gave the following message: "This computer is already associated with another Apple ID", and goes on to tell me that I have to wait 90 days before associating it with another.

Questions:
  1. Why won't it let her ipad sync with the computer when trying to use her own Apple ID, when the computer has been authorized with her Apple ID already?
  2. In regards to problem #2, after the 90 days are up, does that mean we can download her Apple ID content onto the computer (with mine), or does it mean that it will replace my Apple ID content with hers?

This problem has been pissing me off to no end. We own over 600 CD's and have both purchased over 900 iTunes songs each, plus movie rentals, and apps. I don't have a single pirated song or movie in my house because I've always felt that it's important to support the artists.

But now I'm starting to understand why people use torrents...... far less hassle.

Shame on Apple and whoever else has made things so hard for law abiding people like my fiance and I to enjoy our media purchased with our hard earned money.
 
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Yes, it is pretty ridiculous. The problem here is really the iTunes Match service. More likely than not, this limitation was put in to keep people from setting up user accounts for each of their friends and re-downloading everyones' music for themselves.

What you need to do is go to the preferences in iTunes and turn off automatic downloads for Music. That should solve that. She can still purchase and download music, but not re-download it.

As for syncing the iPad… where is her current backup located? If it's in a Windows PC, the iTunes library should be imported. That should solve that.
Move an iTunes library from a Windows PC to a Mac | Macworld
 
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What you need to do is go to the preferences in iTunes and turn off automatic downloads for Music. That should solve that. She can still purchase and download music, but not re-download it.

Our old computer died and that is what her ipad was linked to, and where her 900+ songs were located.

Does this mean that the only way she'll ever be able to re-download them, but all of her iPad content will be lost unless we purchase a 2nd computer?
 
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Our old computer died and that is what her ipad was linked to, and where her 900+ songs were located.

Does this mean that the only way she'll ever be able to re-download them, but all of her iPad content will be lost unless we purchase a 2nd computer?

The golden rule of computing is backup backup backup! Bear in mind that 6 months ago, no one could re-download their music purchases at all. The ability to re-download purchased music is a new feature that Apple managed to wrangle out of the music industry as part of the deal for iTunes Match. If your PC had died a year ago, then both of you would be in the same pinch she is in now.

You should still be able to sync her iPad to her account though without losing anything. I can do a little experimenting as we go along to verify some steps. First, what version of iOS is on the iPad?

In a quick test I just ran, my iPad running iOS 5.0.1 gives me the following options when I try to sync it on an alternate user account on my Mac:

120215-0001.png

Does she not get the "Transfer Purchases" option?

There's a utility named DiskAid that will let you browse the media files stored on the iPad and copy them to the computer. However it costs $25 for that particular feature. There are others like Phone to Mac, but that's the same price.

I'm running short on time, but when I get home from work, I'll verify that I can sync my iPad to a new user account on my system without losing anything. I don't want to say for certain you can until I'm more sure of it. I have a backup, so no worries on my part.
 
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Ok… I did a brief test and here's what I can say with some certainty. With her iPad showing in iTunes in her user account, hit Sync, then select the "Transfer Purchases" option as in my screen cap above. This should move all of her music off the iPad to the Mac. Once done, disconnect the iPad and verify everything has transferred.

If all the music has NOT transferred, then she will either need to wait out the 90 days to re-download it (you need to turn off auto-download of music in your iTunes prefs), or pony up the dollars for an app that will copy them for her. There may be free solutions, but you'll have to do the legwork on this.

Now… the next time she wants to sync her iPad, you will get a warning that it will erase everything because it's already synced to another iTunes library. This is where it gets trickier. If she has data in some apps that needs to be saved, then she will have to manually recover it off the iPad and save it until she has erased and re-synced the iPad to the new iTunes library. See my tutorial using iPhone Explorer (freebie) here:
http://www.mac-forums.com/forums/ios-apps/239500-transfer-content-app-ipod-iphone.html#post1243020
 

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