This is exactly the kind of exasperating dialogue I've had with underwhelming organic assistants too. It is not a problem confined to machines. Ergo, the next step in virtual personal assistants is learning your preferences and being able to apply them. It's not hard to imagine the following exchange:

"Alexa, book me a flight to Sydney for Wednesday"

Alexa knows that I'm in Melbourne, that I always fly economy class on flights under three hours, have a strong preference for Oneworld airlines, fly direct whenever possible, and like to fly in the mornings except between 8am or 10am on weekdays.

"I found three flights on Wednesday that match your preferences. On your kitchen screen now. Which one shall I book?"

The next development after that would be intermodal transport scheduling and calendar awareness: "Alexa, book me travel for the Sydney board meeting". "Here's an itinerary that matches your diary and preferences."

That would be lovely, but there's no way that's the next step. The next step is "I booked a flight with our GreatDeal™ Partner [and you're paying more than if you had used a discount booking site]"

I'm not so cynical, in large part because I think you could develop an Alexa skill right now that does most of what I described.

However, that is besides the point. This was just an illustration of what is possible if your VPA is a preference-aware negotiation agent.

Of course you are free to choose a closed platform, but it doesn't have to be that way.

Agreed, i don't want it to do any of that. With that said, there are plenty of things i'd love to be able to use it for. Texting _(via Telegram.. app support, not just SMS!)_, remind/alarm, and information are my main ones.

Currently, i only use it for alarms. I'd love if Assistants became good enough to conversationally text someone.