I am eternally grateful that I always worked for an employer who always allowed me to carry a sensible amount of fuel.
As bean counters (try to) micromanage that more in the future (and why should anyone believe otherwise, given trends to date?) one can see the misgivings in your post manifest themselves into some difficult realities for more than a few flight deck crews.
One's best self defense is to stay well ahead of the aircraft and the flight/mission so that when these things crop up, there is an out.
Best wishes to all on that score. The "interesting times" are arriving sooner and sooner.