Itunes doesnt update apps automaticaly

hi
Why Itunes doesnt update automaticaly the apps?
after updating from Ipad and Iphone, I "transfer purchases" to my itunes. I click SYNC but nothing.  If I go to check the app windows, some of them shows UPDATE status?? I have to click individually each app??? really??
Is there a good alternative (PC friendly) to Itunes? I cant stand this software anymore
chris

Do you have iTunes 10.5 installed on yur computer?
What happens when you try to update?
If you iPod is 8 or 16 GB it is really a 2G iPod and those can only go to 4.2.1.  A 32 GB one can be either a 2G or 3G. To identify yours see:
Apple - Support - Check Your Service and Support Coverage
Identifying iPod models

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