I just started using OmniFocus, as a replacement for TaskPaper. So far I'm really loving it. But the multiple context issue cropped up for me as well, almost immediately. Specifically, I've run into some roadblocks when trying to use iCal synchronization.
I'm a law student and would like to use OmniFocus to manage my homework/tasks. In iCal I have two calendars, Law School and Law School Events -- the first for my schedule/assignments, and the second for other events (e.g.: Orientations, meetings, etc.). I'd like to use the iCal Sync in OmniFocus to link tasks to those calendars, and I'm not seeing a really intuitive way to do this, as my contexts are rather generic: website, computer, email, scanner, office, snail mail, etc.
This does not provide enough grandularity to easily synch tasks to the appropriate calendars. One solution I've thought of is parent contexts for each of my classes and child duplicates of the actual contexts I want to use hierarchically beneath them (e.g.: Legal Writing : computer, Legal Writing : email, Legal Writing : library, etc.). Then I could tell OF to sync the parent contexts to where I want them. I think this would work, but it seems awfully cludgy, and duplicates a lot of information in a way that would make OF lose some of its elegance. I'd no longer be able to use context view to show me every instance of a task with an "email" context, since there's now five so-labeled contexts and I'd have to check each of them separately.
I'm a bit stumped. If contexts are what you need and/or where you should be to get something done, I suppose I'm looking for a "why am I doing this" tag/context of some sort that I could use to sync to iCal.
Syncing by context seems a bit strange itself. I can't think of any situation where I'd want to sync items in an email context to a single calendar. I email for work, home, school, and pleasure.
Am I missing something here? Is there another way I can do what I want to do that I'm just not seeing?