I tend to agree with the analysis here, and think that Xobni missed a nice chance. I'd be surprised if Microsoft comes knocking again, and I don't see any reasonable way that they can build their tool into anything that is not parasitic on Outlook, much less effectively monetize it...
They could license their product to large businesses for more money than you think it's worth. Even if they save users 10 minutes a day, do you know how much an executive is willing to pay to save 10 minutes of frustration?
Any extension to the Microsoft Office suite should just be marketed straight to enterprise customers. More hours are spent looking at Microsoft Office every day than probably any other activity save sleeping. It's a huge market filled with deep-pocketed customers.
Then the best business model available to them is to get bought by Microsoft.
This is not a bad business plan, by the way-- there are quite a number of folks who have made good money filling some gap Microsoft missed, and getting acquired.