My startup, reclaim.ai, does a lot of that -- except for the O365 part (for now). We do a special kind of syncing that protects your privacy and if you use Fan

My startup, reclaim.ai, does a lot of that -- except for the O365 part (for now). We do a special kind of syncing that protects your privacy and if you use Fantastical (which supports Reclaim), it'll intelligently merge the opaque blocks together to make it appear as one. Give it a shot and let us know what you think :)