I am using Outlook 2011 for Mac now since one week for GTD. Switched from Outlook 2007 on Windows 7. What you might like:
* The "my day" window is nice (cmd+9). It shows today's calender + tasks. You can insert new tasks quickly with ctrl+shift+t. Then enter the task description, then shift+tab 3 times and type the context. It autocompletes. Quite handy.
* In the "my tasks" view (cmd+4), configure to show only those categories representing your contexts (Categorize -> Edit categories), in the navigation pane on the left uncheck all categories, then check the one you want to look at. Sort alphabetically.