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I've been using vdirsyncer to keep CalDAV servers in sync. It works with basically everything. Works great with khal but I've always wanted a month or week view so I'm gonna check this out!
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In addition to the question around integrating with GCal/Outlook, would it be possible to tie into other task management tools, such as taskwarrior?. Seems almost like a logical extension, in that both are attempting to cover that same space.
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While I don't know if it will make a difference, there was noise on the remind mailing list within the past week of a new release (1.5.0) of wyrd. I'm not sure it will resolve your issues, but if you have narrow-terminal (how narrow? < 80 chars?) issues, you might report it there.