I know some people have managed two way type stuff using Telegram but I don’t know the details. I suspect if you were using something custom like a Google AIY or Orange Assistant or Mycroft or Snips you could set up a conversation like this.
The limitation isn’t on the openHAB side so we can’t really fix it. The limitation is on the GA side. Alexa may be more flexible too, I don’t know.
I´m pretty sure this will come very soon. (within the next 1-5 years).
The issue is, atm the devices isnt suitable for asking questions. They are meant to answering questions and doing tasks. But I see no reason why they shouldn´t be able to ask questions as well. Only problem is - What questions would you like…
You´ll either have to predefine all kinds of questions which suits you. Or the device will have to learn all about you as an individual. (the last option is the one which can/will become a huge problem for most people, since this is what people dont seem to want due to ethical and private matters).
At the moment I dont see why the use of routines shouldnt be able to handle the pre-defined questions very easy. I´m pretty sure Google have already thought about this long time ago. They just need to “open” this feature. They already do have the “continue conversation” working.
Like Rich said its already possible it’s just how do you go around doing it I personally would prefer it all too be ran locally and step away from Google or amazon it would just take an immense amount of time writing the responses ect as you say I would prefer too predefine the responses and inputs