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I do have one quick question though: if I end up having to re-download all my apps, how do I go about downloading for free and app that I already paid for? I have never done this.

If you've downloaded it once you can keep downloading it as many times as you want. Lets say you accidentally delete a paid app from your iPad, you don't have to sync it back from your computer, you just go to the App Store on your iPad and download it again for free.
 
I do have one quick question though: if I end up having to re-download all my apps, how do I go about downloading for free and app that I already paid for? I have never done this.

That's not really a problem ... Apple knows what you've paid for on your Apple account ... you'll get a message saying something like: You've already downloaded this item, are you sure you want to download it again? theres no charge since you have already paid for it.

A bigger problem might be trying to remember everything that you have already downloaded.

But, if you connect your iPad to your computer, wait for the icon to appear representing your device, click it ... look for the Apps Tab ... click that, then just recheck the boxes beside all the apps you want on the iPad ... then it will transfer them to the device upon syncing ... even if backup/restore did not work.

you're good ... just takes some pains to get past the initial set up ... that's all.
 
Upgrade both iPads to the same iOS version, then do a backup and restore. There's no garbage or strange changes that could affect your new iPad2, as both have the same version of iOS.

It's plain simple.

This is not like moving from a PC to a MAC, you know...
 
Do I need to re-purchase iPad Apps if I get another iPad?

One question I don't know the answer for, and I'm sure the OP wants to know as well:

If I buy another iPad (in addition to the one I already have), will I need to purchase the same apps again, or will I be able to run the same app I have already purchased on both?

OOPS! Sorry If this answer was already discussed earlier...
 
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One question I don't know the answer for, and I'm sure the OP wants to know as well:

If I buy another iPad (in addition to the one I already have), will I need to purchase the same apps again, or will I be able to run the same app I have already purchased on both?

OOPS! Sorry If this answer was already discussed earlier...

you will not need to repurchase apps for multiple iDevices ... just make sure you're using the same iTunes account.

either syncing the new device via iTunes, or directly downloading an already purchased app will not charge you for the new device.
 
Transfer iPad 1 Apps to iPad 2

You'll be able to sync your apps from your computer's iTunes to iPad2 (the apps will be compatible). You could also use the iTunes backup of your iPad1 to restore onto your iPad2 (so that you can have their settings/stats/content). You can't sync directly from one iPad to another.
 
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