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I think you are looking for a tablet. I don't know of any e-readers that can synch with outlook and office.
If you can check your email and calendar online, then maybe a Sony 950 or a KDX. They both have 3G so you should be able to check your email using the provided browser.
The Sony 950 has a 7 inch screen and Sony is known to have the best EPub support with reflow and the like. I know nothing about the Sony browser. I am not even sure that the 3G allows you to do anything more then connect to the Sony store.
The Kindle DXG has a 9.6 inch screen which makes reading PDFs a bit easier. It does not have PDF reflow and you cannot take notes in a PDF. The browser is a bit slow but useable.
I would guess that a rooted Nook Color would be good for you. I don't know about its PDF functionality but it will be your best bet for using outlook and a calendar. The color screen might help with reading charts and the like.
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