No, you are never prepared enough, is the simple answer.

The guy who went hiking and cliffed out, took a risk, but he stopped when he was in over his head and he rescued. He stopped when it was too risky, he stayed put and signaled.

The guys on Hood got overwelmed by a variable outside of thier control and things went down hill. Bad luck, compounded by over confidence and lack of means to signal.

Kim did a lot wrong except keep his kids alive, and that was probably as much his wife as him.

My oops were compounded by over confidence, lack of equipment, and poor planning.

So no, you CAN'T be prepared enough. But what you've seen have been after action analysis of the events. Those are supposed to be complete and detailed, so you know what went wrong, how it when wrong, and what could have been done to make it better. It's called learning from another's mistakes. And when you screw up enough, we aren't going to be subtle. As I might have said other places, if I die due to an oops on my part, I want this forum to disect my last actions to see what I did wrong.