There's nothing wrong with going for incisive questions. It's just that Cuomo isn't very good at it compared to Matthews in his prime for example. Like I said, he just meanders off into tangents and gives his own opinions instead of getting answers out of guests. I get most of my news from NPR and reading articles on google news anyways, so maybe I just have a low tolerance for all the talking heads.
I wish we saw better questioning from the White House press too. Every time I watch though, Trump either talks over the reporters he doesn't like, doesn't answer their questions, monologues so reporters can ask fewer questions, or threatens to kick them out/call them fake news. So that's why we haven't seen too much push back in the press conferences unfortunately. It's almost suppression of freedom of the press.