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Updating both IPhone 3GS and IPad2 at the same time

How would I go about updating both devices from the one Itunes download? In the past I would have to download what appears to be the same update twice in order to install it on both devices.
I am planning this in anticipation of the new ios5 update.

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Due to the fact that the iPhone and iPad use different files, you will always need to do two downloads.
You can transfer the purchases from both the devices to single itunes and update the purchases to all devices through manual app sync. In iOS 5 you will get an option for the wireless sync the apps you downloaded with your itunes account (to all devices with the same account ) through iCloud.

Or if you have a jailbroken idevices, you can use any of the below apps to sync multiple devices wirelessly with your devices . These apps are available in Cydia store

Wi-Fi Sync
Effortless Wireless Sync
iPhone to wirelessly sync
Due to the second post I just wanted to clarify that I thought your question related to the updating of the operating system known as iOS on your two devices.  If this is your question then there are 2 different files that need to be downloaded.

If you are talking about APPS, then that will depend on when the App developer actually releases an update.  The App developer has had a copy of iOS5 for some time now and may have already released an update in anticipation of iOS5 coming out.  But normally iphone apps should work on both devices, and iPhone / iPad apps too.  The only ones that will not work is if it is an iPad only App.
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