Well, there are people here way more qualified to answer most of your questions.

My advice is to be careful of using the word "hacking" as its meaning has changed, and means different things to different people. An old fart such as myself would take it to mean possessing considerable skills and knowledge together with the ability to produce innovative workarounds.

I believe that what you are describing is more correctly known as "wargaming"?

As a general thought, I still believe that batch file processing still has a place, and is worth learning.