You can, but I don't want to. It takes longer than reading, makes me sit and actually listen, and it just feels awkward to me.

That's certainly true for most people sitting in front of a computer but I really liked the inclusive design guidelines from Microsoft[1] reminding us that there are many people for whom any particular assumption is untrue, often only temporarily or in a specific situation:

https://www.microsoft.com/en-us/design/inclusive

As an example, a coworker mentioned that his use of Alexa went from casual to heavy when they had a child and the ability to do things while carrying a baby suddenly became really important. I suspect there are more situations like that than we might think at first.

1. I know, 90s me is still getting used to saying that too

And I know a couple with a relatively young child and they love their Echo. All the tell a joke and other things along those lines that are kinda dumb to me. Or questions that I'd just as soon type on my phone or a computer but which are more natural to just speak in a family conversational setting.

I think a good model to imagine is that you don't have any computers on you and you're talking to an assistant over the phone who has access to Google and other online resources. The types of responses you'd expect from that at least modestly intelligent assistant are probably not all that different from what you'd like to hear from a digital assistant.

If I were to ask a question that had a long list of potential responses, I'd expect them to ask me to clarify or narrow down what I'm looking for or at least explicitly ask me if I really wanted them to read the whole list.

I'd expect my assistant to know a fair amount about me and the current context. Using those clues a human can pick out what I really care about, at least in most cases. Even when there is a list of responses I'd expect an assistant to give a better summary when asking for clarification.

Certainly learning my preferences is an important component of a personal assistant. e.g. I almost always go to the airport using a particular service.

That said, for those of us who don't have personal admins, there's a lot of opportunity for digital services that fall between purely self-service travel booking as it exists today and and having an assistant.