I have a theory on why Siri sucks so bad. It's not the ability to build an excellent AI/ML service. It's the poor leadership and the present-day Tim Cook culture that won't allow them to do what they need to do. So, those in leadership/management positions just throw their hands up and collect a check until they're given a nice severance package to launch their own startup.
Alexa got way better later. So it is meant to be the current Alexa leader. 5 year old tech is ancient tech. As you can tell by all the rave reviews of Alexa she is doing a far better job than Siri is.
I’m using Siri on a daily basis and have no major issues with it. Especially if you realize that Apple is pretty much the only party who focuses on and cares about privacy. I tried asking the same questions as you, only in Dutch. The first question goes just fine (How old is Barack Obama? / Hoe oud is Barack Obama?), but Siri immediately fails at answering the second question. So yeah, the complexity you’re describing is pretty much non-existent on my side.
But how will the poor guy get siri to tell him how to get home? Hold on... She'll tap you when she's ready bro.