It appears that Orange is now offering a bundled plan for the iPhone 4 and iPad 2 which runs at a combined price of £65 per month or around $106 US Dollars. This bundled plan limits users to 2GB of data, which is a little low...5GB of data for both devices would seem more justified. This data plan includes 600 minutes and unlimited texts.
Basically, for a new customer the cheapest deal available would get you a 16GB iPhone and 16GB iPad for £149 ($243 US). The most expensive deal - for a 32GB iPhone 4 and a 64GB iPad 2, would set you back £349 ($570 US).
I am planning to pick up the iPhone in the next couple months (dependent on the release of the iPhone refresh) and would certainly be interested in sharing the data across both devices. Separately I probably spend $140 per month on data on my iPad 2 and Android smartphone. My 1st generation iPad was a WiFi-only model and was tethered to my Droid for internet access...essentially running my smartphone battery down rather quickly.
I feel that bundling a data plan on both a tablet and smartphone could be successful if/when Verizon or AT&T decide to offer a bundled plan. It certainly wouldn't include unlimited data, but the limits need to be in the 5-10GB range.
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