Me too I started with the GTD set-up on Outlook. Then as I saw it not so fast in managing my tasks, I started to appreciate web solutions like Toodledo. More quick and easily integrated with outlook as you can send to yourself mails that will become tasks in Toodledo. If today, I'd forced not to use a web GTD system I'd consider first to use my personal internet key or alternatively to use my Android device where I have all my tasks sync with Toodledo, thanks today to Ultimate To Do list.
Let's take in consideration therefore that toodledo can sync with outlook. I used at the beginning Chromatic dragon but today there is one more you can find here:
toodledo&outlook sync


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