I am new to GTD. I am considering purchasing the Outlook add-in but have also been reading the white paper on setting up Outlook 2007 myself. What are the pros/cons of using the add-in? The cost isn't a factor.
I bought the Add-In instead of a dyi. Figured it would take me a couple of hours to get it by hand, and I still might not do it correctly. If your job or life require the ability to reconfigure software by hand, or if the concept is intrinsically interesting to you, then maybe it's worth a dyi. But if the price isn't an object then download, install, and you're right back to GTD
Another key consideration is the volume of email you get. If you are at or above the 100+ per day, definitely go with the add-in. It's primary advantage over the white paper implementation imho is it's ability to speed inbox processing.
I have tried the diy from the Outlook 200* whitepapers and find the add-in to be the more efficient and helpful way to integrate with GTD. Not only are the contexts right there, it was very easy to create new projects. I agree with jpm that if you have a number of projects and/or a large volume of email the add in is the way to go.
I'd go for the add-in. It's really simple to use. Make sure you watch the video tutorials they have. I didn't and was using the add-in incorrectly for months. Now that I know what I was doing wrong, it's dead simple and I wouldn't go back to just Outlook.