On the transition thing, I can't say that moving from a D5 to a Z6 and Z9 for topside use was anything approaching traumatic. One of the biggest (and most annoying) changes was remembering to press the shutter before looking through the viewfinder. The rest have been pretty minor.
But I do think Massimo is right: if you have something that works and you get the results you want, why change it? Yeah, I love the flashy new toys and the thought of some of the capabilities. But really, will the new tech help me take better pics? Marginal. I really have my doubts. It's the same bloke behind the camera. With a D500 I can't say I need faster AF or more pixels; I do like the idea though of reviewing an image in the viewfinder.
I'm no Luddite and thought the Spinning Jenny and the Ravelling Nancy were wonderful developments. Sure mirrorless will be the way to go for the future underwater (as it is now topside). When I need something new as the D500 system is either clapped out or there is something dramatically new, it'll be mirrorless. Till then, hello D500, my friend.
But if I was starting from scratch now, yep, I'd be checking out mirrorless options.