VB6 was the worst and best kind of software. You were NEVER (even as a professional) sure if it ran on the other/target machine, so you just hoped for the best.

Also, I quite like the cat-and-mouse analogy you mention, because I feel it was (mostly) a harmless way to hone skills, to level up knowledge essentially, with a (at the time) reasonable amount of risk involved, which kept it exciting enough to learn more. It would be cool to see schools have a bug-bounty type of environment here or there, just for those few kids who actually want to spend their time on getting better at networking.