It's not the same everywhere. I'm always impressed by the tactical questions and more intelligent questioning that Dutch/German journalists employ, and while it's more uncomfortable over here for managers to explain themselves, it's pretty accepted over there.
England seems to be unique in having the most boilerplate post-game questioning of any footballing culture - 'So [manager here], what went right/wrong for you today?', 'did they just want it more than your team?', etc.
Even Italian journalists have more variety - some subscribe to tactical questioning, others buy into an exaggerated celebrity culture and spend their press conferences asking about off-field drama.
What grinds coaches down in England is, as you say, the monotony of the questioning. Same basic questions, same brainless storylines, over and over, for 150-200 press conferences, interviews, etc., every single season.
But, at the same time, it would be interesting to see how Ange handles tactical questioning a la Germany/Italy. 'Why do you insist on inverted fullbacks when your best wide-player, Son Heung-Min, is at his best cutting inside rather than isolated on the wing? Why is there such a gap between the midfield and the forwards?', etc.