Joking aside, I'd say HQ Trivia are getting savvier with the questions. A final question the other day was along the lines of "Which two female artists collectively have the same number of Grammys as Beyoncé?" with the answer being "Adele + Madonna", I believe.
Those are generally rare questions though because difficult questions for bots are also difficult questions for humans. HQ can't have too many of those questions without degrading the player experience.
Because of that, I don't think we will ever get beyond 10/11 questions right per game. That still leads to a decent chance at winning at least one game per week though.
You are right about the experience issue, though. It feels almost like they're trying to make it so you can't win with questions worded in that way, since even someone who actually knew the numbers of Grammys all the artists listed had would struggle to add them together in time.