Updated Apps won't Sync

In the past couple of weeks, I've run into an issue where my iPhone 4s and iPad 2 will indicate that there are available updates to apps on the device. This is indicated by the red badge that appears on the App Store. I open iTunes, download all available updates, and proceed to sync my iOS devices. The sync finishes without any error messages, but the updated apps don't get pushed to the iOS devices. It doesn't matter if I sync via Wi-Fi or USB, updated apps aren't being synced.
If I update the apps using the App Store app on my iPhone or iPad, the updates are installed successfully. If I delete the app from my iPhone or iPad and then sync with iTunes, the updated app is synced correctly.
All other media (music, videos, podcasts, photos) is synced as expected. I can't figure out why the updated apps aren't being applied during a sync with iTunes and it's driving me crazy. I don't want to have to use the App Store app for updates. I just want to use iTunes like I've always done.
Both devices are running iOS 5.1.1. I'm running iTunes version 10.6.3.25 on Windows 7 64bit.

I have exactly the same issue, but with the latest Apple equipment...  New iMac, Yosemite OS, and iPhone 6 Plus.  Did you ever get an answer? 

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