I've had my head in chatbots for the last few months. There is so much potential. We've created one to help supplement the experience at an event at Sydney Opera House, an experiment for a retail experience, and I just created one to help answer questions people had about the arrival of our 3rd child (that last one was for fun).
Managing expectations - as soon as you say bots and artificial intelligence, people think they're going to get a human experience from a robot. We're way off that. The learning functions in api.ai and wit are great, but they're reactive, not proactive. People will still assume they can ask anything or speak human and the bot will respond. Best thing to do. Treat it like a robot. Reminds me of when working at Ask Jeeves. People thought that asking questions was the best way to interact, because it was 'Jeeves'. Reality, it pretty much ran off keywords.
Logic - it's easy to get carried away with what the bot could do. There are 2 types we've been experimenting with. Multi Q&A. Single questions with pre-programmed answers. And structured flow. Where eseentially, we take people down a path and keep the branches as simple as possible. Otherwise you end up in a test and fix merry go round without the confidence to share it out.
Manual - if you're bot's in FB messenger it's really easy to keep an eye on conversations (not on a huge scale of course) and be able to manually jump in and answer questions, while still capturing them and registering answers for any similar questions in future.
Personally, I think bots will become the standard for transaction of information in future. Up to now, that standard has been forms. Forms are definitely better than they have been but they're still forms. The faster horse if you like. Bots are the car and they'll be hear to stay. Just my opinion though -would love to debate it.