IT Toolbox has a great little summary of the experiences of Mike Kavis, a guy who's been living Microsoft free in an all Microsoft shop - at work! It all started from an "eat your own dog food" challenge (something i did with my wife which finally precipitated the switch to Linux on her part). Check out his other articles in the series:

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Linux Journal has an interesting article about how to set up Linux for your grannie. There are some great ideas to consider there.

CNet has a great article highlighting Free Software alternatives to various popular proprietary products. Good reading, balanced coverage of strengths and weaknesses.