I hear you... That's why even with the GTD plugin for outlook it still
falls short on the handheld as well. As I noted on another thread, I
sync to a Treo and a project I recently created syncs as a blank Todo,
no associated data and no tasks could be linked.
I really like the plugin for mapping plan of action, but could just as
easily do that stuff (though not with the auto alarms which outlook is
actually weak on without the plugin) manually.
As a Mac guy forced to work in Windows for a project I am on, I've
found Outlook horrible in many ways - Entourage seems much more
thought out, though I actually use Thunderbird for mail. The only
thing I actually like Outlook for is the calendar which is quite nice.
I really loathe it as a mail client. Sorry got off topic there...