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Aside from the iCal stuff, which I don't use (I haven't really investigated integration yet) I totally agree with what you're saying -- I also struggle with the whole way due dates are set up. I currently have three sections at the beginning of the projects sidebar that just list the projects I have to remember to work on daily (for indefinite periods of time -- like exercise, etc) and then upcoming projects with a due date that I have to remember is coming up) These lists just state the project and when it's due and if I want to know more details about the project, I have to go into a separate category. A lot of this would be taken care of by the system you suggest.

OmniFocus is already so good at coming to you where you are, and helping you manage your tasks in the way you naturally think, that it would be great if this issue were addressed as well.