It's really simple, you need to convince the people holding the purse strings it's worth their money to spend inordinate amount of time on a problem affecting a small portion of their desired demographic. Getting Devs to work on antiquated machines will just make their lives miserable.
IMO it's a dynamic equilibrium, with too large resources you'll accept sub optimal situations. Think Google c++ build times. I agree living below acceptable conditions is unnecessary drag but it's good to wave back and forth. An exercise in awareness.
Not for me, I don't get extra time to fiddle around shaving milliseconds, my environment is so slow it's all I can do to get working software out the door in the timelines I'm given. I have solutions to improve the speed of my software and environment, but they take time to implement, time that I could be working on features that make tangible differences to the bottom line. Guess what gets priority?
If it were up to me, I'd spend this entire year refactoring, but it's not.
