I am facing issues with my music on my iOS device. I have five devices connected to my apple id. And out of which a Windows Machine and iPhone is not able to sync the purchased songs on the the Windows machine and the iPhone.

I am facing issues with my music on my iOS device. I have five devices connected to my apple id. And out of which a Windows Machine and iPhone is not able to sync the purchased songs on the the Windows machine and the iPhone. The iPhone4 shows the songs are not supported and on the Windows Machine the songs do not play completely. Can anyone advice what could have gone wrong ? Because rest of the devices are synced to MacBook and they are able to sync the content normally.  I have even subscribed to iTunes Match but the problem is still not fixed.

Firstly...  a little Clarity...
Devices refer to iDevices... iPod... iPhone... iPad. ..   Not Computers.
Authoriation applies ONLY to Computers... of which there is a Limit of 5 per Apple ID.
If the issue is with iTunes on your Windows Computer... Perhaps you need to Re-install iTunes...
See Here... to Uninstall and Re-Install iTunes...
http://www.apple.com/support/itunes/install/

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