Why is my iPod losing its apps?  Why can't I sync them anymore?

Why is my iPod losing its apps?  Why can't I sync them anymore?

What apps?
When do they get "lost"?
What model iPod and iOS?
Many developers when they updated their apps to support iOS 5 and 6 dropped compatibility for iOS 4.2.1 and earlier.
Do you have any Restrictions set that would prevent installing them? Settings?General>Restrictions
What happens when you try to redownload them directly to the iPod (if the iPod has iOS 4.3 or later)
Downloading past purchases from the App Store, iBookstore, and iTunes Store

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