ITunes 10.6 not syncing purchased music to iPhone iOS 5.1

I upgraded iTunes to version 10.6 and my iPhone to iOS 5.1. iTunes will not sync purchased music from the iTunes store. In the past, I have been able to sync these purchases via iTunes. Now they appear greyed out on my iPhone 4S.
When I go into the App Store from my iPhone, I am able to download my purchases, but there are many and tapping on them one by one is not something I want to do EVERY time I update my iPhone to a newer OS. I would like to sync from my computer since those files are on my computer and I can play them in iTunes.

I have also tried adding my music into a different playlist and it will still not sync half of my songs. I have also deleted the Purchased playlist and copied them back into it again... still nothing works
This is quite silly!

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I'm hoping someone can offer some advice. Since upgrading to iTunes 7.5 and Vista, I've noticed that my iPod classic and iTunes are no longer syncing the Music folder in my library. I've been able to repeat the following behavior:
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After having to get a new computer, I tunes repeatedly asks to authorize the computer to play/sync purchased music. However, ITunes is saying that the computer is already authorized. What do I do?

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