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if there is no new feature on iOS 5 that you will miss if you don't upgrade your device, then I recommend not to do it.
 
I reckon iOS 5. I'd NEVER "JB" any of my iOS devices. Make it simple and you would enjoy it more than what you used to be :)

PS: iOS 5 can update the software without having to plug it to iTunes, this is a very nice feature and you can use this feature ONLY if you iDevices are not Jailborken ;) + use can use iCloud NOW!
 
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I'm going to stick with my jailbreak for now. I'm not seeing any must have iOS5 features for the iPad -- most of it is just watered down versions of features I already have. Then, the most interesting stuff (Siri & Geofencing) aren't coming to the iPad anyway.
 
I'll be waiting at least a few months, though I may eventually give in if a JB for 5 doesn't happen. But there are a few tweaks like Dimmer and some activator stuff that make my life so much easier. I spend most of my day (and night) with the iPad in one hand and a baby in the other, so little changes make a big difference.
 
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