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I like to use keyboard shortcuts as much as possible.

Does anyone happen to know of an application that will allow me to have a task selected that would allow me to change the Context of a task? Like pressing "cmd-w" or whatever and have the context changed to Waiting?

I'm thinking a TextExpander key-combo might work, but before I spend any time on this, I thought if someone is already doing this.

Well, one could write an Applescript that changed the context of any selected task(s) to a prearranged value, and I believe there are a number of programs which will allow you to bind scripts to keyboard shortcuts. FastScripts by Red Sweater Software is the one I've used at times. But for this particular application, the built-in smart matching for project and context names may be all you need. If you only have one context whose name starts with a 'w', typing a 'w' and pressing return while in the context field will set the context to that. It also gives you a list of everything that matches, so you can quickly narrow down the list if more than one does the matching is done against the whole string, but the characters matched don't have to be a substring, just occur in that order, so "wf" would match "Waiting For" but not "Wait list" or "Forest of the Wookiees".
Sounds good; I've had success following what you've described using textexpander & smartmatching on the various fields, so I'll stick with that process - probably the easiest to implement since I'm comfortable using textexpander.

Thanks for the feedback,

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