Am curious about some practical aspects of the KITW system Mark recommended.
Say you've got a long list of folks who you want to keep in touch with. You're using CTRL-SHIFT-K or whatnot to create a recurring task for each person in Outlook.
1 - How do you verify that everyone in your contact list has a corresponding KITW task?
2 - How do you verify that you don't have multiple KITW tasks for the same person?
I've just finished setting up a pretty similar system in Gmail (thanks PierG for the idea... perfect workaround, if you don't mind the manual labour involved), but (1) and (2) above both strike me as potential headaches going forward.
Not that having too many reminders for a person is necessarily a disaster, but I like things to be systematic.