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Whoops...I wasn't clear enough.

What I'm trying to do is much less precise than it sounds.

I'd like to be able to say things like, "I'll have that to you at the end of next week." To say that, I need to look at what else I'm planning to do this week and next week. Just a list of tasks and days, something that I will determine myself rather than something that would be programatically determined based on workload.

I would look at the schedule and think, "I've got a lot going on this week, I can't promise anybody more stuff this week."

Or, "You want that by the end of this week? OK, I'll have to put off these other things that I was doing."

A calendar-like system that I can drag and drop tasks around would be just about right.

I'm thinking that I will experiment more with doing this entirely within contexts, and possibly write some AppleScript to move things around and/or rename them.

In other words:
Contexts for "Today (Tuesday)", "Tomorrow (Wednesday)", "Thursday", "Friday", "Next Week" which would contain "Monday", etc.

Daily AppleScript would rename "Today (Wednesday)", and move the tasks around.

Would also need an "Overdue unfinished" context that would collect everything that I didn't tick off.

I'd need a carefully crafted perspective for doing this, since some tasks would need to be done in order. But, realistically, my stuff here is *not* that complex, I just want to look at my week and say "I can do more" or "Wow, I don't know if I can get this done" and warn people.

The challenge, of course, is to do this without spending so much time building the tool that I would be more productive if I simply sat down and worked. :)

(When I'm a billionaire, I will have productivity software that works precisely how I want it to. :)