It would have been great that these questions were asked. And the interviewer and her team should have been able to plan similar questions for the show.
But there might be a good reason why your kind of questions were not asked.
Although my experience in Canadian politics is 30 years ago, it was common practice for a high-ranking politician and the media forum to enter some kind of negotiation prior to the public one-on-one interview. If the politician does not get the right terms, he/she turns down the interview. They should not set themselves up for a public ambush.
The fact that the audience was a pro-Trump crowd, disguised as average voters, tells me that the makeup of the audience was one term of the deal. In other words, a negotiation did happen. Mr. Trump's team got the audience condition.
The line of questioning was likely another agreement between the two parties. Mr. Trump's handlers knew the questions in advance. They knew Mr. Trump would be able to handle them in his unique way.
If your kind of questions were put on the list, the handlers would have demanded a total changeout--or Mr. Trump would not have walked into an interview disguised as an ambush. CNN would not have got its political show.
We could say that CNN got ambushed instead. But they knew what they were getting into. Softball questions would turn the event into a Trump rally.
What I would like to know is: "What happens when the media outlet does not follow the agreed line of questioning?" I wasn't high enough to know about all the terms. I wasn't around long enough to experience when the media goes against the deal.
There should be no doubt this interview was mostly an orchestrated event.