Could you expand upon the technical problems you ran into? I would have thought it possible to build a reasonably good meeting scheduling bot with just classical constrained optimization algorithms (no AI / ML), but I'm probably missing something.
Well, for starters we are looking at question answer type natural language processing, something superior than Google smart replies. So imagine a flow something like '<Bot>, schedule a meeting with <p1> at Noon tomorrow. Now the <bot> has to figure out the availability of <p1> at Noon. This is relatively simple if <p1> has given the bot access to the calendar but that's unlikely. So the bot has to start a series of dialogs which to figure out the availability. Now you are looking at NLP + some state maintenance and it gets even more trickier if you have more than one participant, if there are no available overlaps, if the bot has to force a schedule which is dictated by the boss. Using a phone app you can solve some of these by prompting custom keys but then you run into app distribution challenges.