I read The Cuckoo's Egg only a few years ago (in my 30s) and it's an absolute delight. Easy to understand if you do any sort of linux administration, and really demonstrates how lax things were and how far we've come in terms of cyber security.
Yep. I've found that the ticket or tech debt isn't important until it becomes on fire and must be fixed ASAP. It doesn't matter that the possibility for the bug to happen has existed for 2 years, the organization doesn't find the investment worth it until it's burning down the house.
I think we're starting to see that across the entire industry. Leadership is easy when times are good. The job has gotten very hard.