Apps - Download All Free Updates - You have already purchased this item

I have an iPad and iPhone, and over the past few months I've noticed that iTunes keeps getting confused when trying to download app updates.
So right now if I run iTunes, it shows that there are 16 updates in Apps.  I click on Apps and then click the "16 Updates Available" link at the bottom right.  This opens the "My App Updates" view.  I then click "Download All Free Updates" and get a prompt that says:
You have already purchased this item
You have already purchased this item but it has not been downloaded. To download it, select Check For Available Downloads from the Store menu.
This is confusing because:
I have no idea which of the 16 app updates it is talking about
I'm not told why it has not been downloaded
Check for available downloads doesn't do anything.
I can get around this problem by manually downloading each update individually, syncing and trying an update again.  But after a few weeks I get more updates and the problem starts all over again.
Any ideas why this is happening?
Cheers
Boz

You read a very old article that applied only to apps.
Redownloading is quite simple
Downloading past purchases from the iTunes ... - Support - Apple

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