I mentioned this is another thread but thought a more general post was also appropriate.
If you've not looked at the new addition to the Microsoft Office Suite, One Note, you may want to (there is a trial version included in most upgrade packages of Microsoft Office).
One Note is not just for Tablet PCs. It is a free-form work organizer that lets you consolidate in one place all the documents, files, notes, etc related to a topic.
You can use One Note to do your project planning (as an outline or as freestyle notes). Then, when you are ready to move something to a context list, you can highlight it and with a single mouse click turn it into an Outlook Task.
Also, when One Note is not running, an icon appears in the system tray. Clicking on it produces a utility program called Side Note that lets you enter notes into your One Note files, and you can create an Outlook Task directly from the Side Note window as well.
I'm still playing with it, but it appears this program with its seamless integration wth Outlook provides a way to do project planning and still send only the Next Action to Outlook to appear in the appropriate context Task lists.