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Take myself I stopped using Outlook because it made absolutely no sense since I would use only a portion of what it offers - the rest would be nothing more than bloat. That doesn't mean though that I switched to a web based solution like Gmail - that won't happen - instead I use an excellent email client called InScribe. so any solution that ClearContext or any of the other entrants in the field would be of no use to me.
I don't pretend to know the solution to this problem but I think it is something that is beyond anything that a plugin will be able to fix - the marketplace for email clients is just too big to be able to cover all the bases.
http://www.gaborcselle.com/msthesis/
Building ML/AI-based systems to do these things is hard to do really well.
I think that so many of the fundamental things about the way you access your email are broken. For example, the way you view your email - a time-sorted list of incoming messages - hasn't changed in the last 20 years.
However, the way you think about email is not as a time-sorted list, but as an amalgamation of people, relationships, files, and conversations. At Xobni, we're fixing these things first, before moving on to fancier things. Watch out for more :-)
Gabor Cselle
Even as a non Outlook user though I do keep my eye on what both companies are doing if only from a general interest POV.
I don't know where you drink but, around here, the strippers take FAR too long to shed their g-strings.