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I have been known to tell people that often times, Outlook is just not worth the time.  I use to POP out my email to Thunderbird(the open-source equivalent to Outlook), but then I stopped doing so when I realized how much easier it was to just use the Gmail equivalent.

Here is a good article that puts the two against eachother.  To each their own.

http://lifehacker.com/398778/outlook-vs-gmailthe-definitive-comparison