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Chris, I have also...
Chris,
I have also been struggling with the heirarchical view of tasks. I have not found the ideal program. I am toying with writing my own, but lack of time/skills at this point have stunted my efforts. A number of programs are close, particularly life-balance or bonzai (windows only).
But it would seem to me that the ideal app would view projects as outlines with lots of abilities to attach relevant documents, links, etc. as Omni Outliner does, but then make any given point or particularly subpoint a task that could link immediately to whatever PIM program (entourage or palm desktop) that you use with its context (calls, email) etc intact. I have other thoughts about this, but I haven’t found anything that quite does this.
interestingly, if you make outlines in MS Word 2004 in the “notebook layout” view, then any point in an outline can be made into an entourage task. However it is not given the category info as far as I can tell.