Are there any guidelines on what is considered, for example, too tasking for system to clean up?

No difference. Whether you kill the process with a few bytes of allocations, or 10Gb. In fact, AFAIK the way most operating systems work, if you allocate memory and then free it properly, the OS will still keep that memory 'allocated' to your process, because you're likely to ask for that much again. Again, talking about killing the process. While running, you're right, memory leaks are a huge deal. Especially for long-running applications and services.

a lot of my reading into people disagreeing with me probably stems from my background.

I think a lot of programmers fall in the same category, myself included. Analytical intelligence and social intelligence tend to have an inverse correlation. I probably didn't develop the social skills most people acquire by high school, until some years after undergrad. And I didn't learn to take things in general less seriously until my late twenties. I think that's just part of getting older, learning to get along with people, play politics. Learning to take enough enjoyment from conversations with nice people, to tolerate being nice to mean people. I'm still not where I'd like to be. I think we're all still learning. So ist das Leben.