Kinda the same, but for me, it was more of a gaming-driven motive. I learnt the basic DOS commands my observing my cousin, so I could run Prince of Persia, GORILLA.BAS, Dangerous Dave etc, even when he wasn't around (it was his 286).
Later on, when I got my own PC (a 486) I got into scripting by customising my AUTOEXEC.BAT to display a menu so I can jump into my favourite game immediately after the PC booted. Of course, I also learnt about TSRs, conventional memory, tuning CONFIG.SYS etc just so that I can run some tricky games like BioMenace and OMF2097.
I event learnt basic networking and made my own null-modem cable, because I wanted to play OMF2097 with my friends without sharing the same keyboard (we would always fight over who gets to use the right side of the keyboard, which was obviously the best side).
The first time I dealt with a virus was when I tried installing Prince of Persia 2 from a set of floppies I got from my friend. Dealing with the virus (it was one that "melted" the screen) unlocked a whole new world of malware research for me - and collecting malware became one of my hobbies. I also learnt hex editing and some assembly language because I wanted to cheat in Prince of Persia 2, and unlock shareware programs like Cheat Machine - and what I saw within the hex code of Cheat Machine blew me away, it opened another new world for me.
I built my first PC (a PIII 450, along with my first GPU - an nVidia RIVA TNT) - all parts carefully selected, so that I can play games with the best performance for the price.
In the Windows world, I was endlessly tuning my PC, diving into the registry, switching kernels (yes, there were thirdparty kernels you could install), even optimising file layout on the disk - all so that I could get the best gaming performance. I dived deep into scripting with AutoHotkey and Perl to make macros, bots and other random utilities for the games I played. After that I.. well, I could go on, but you get the picture.
So while DOS was my starting point (and a most fond memory), it was ultimately gaming that I owe my career to.
I started with c64 but stuck there with basic ( extension port was broken unfortunately could not dive into assembly there )
Then I got from someone an old 286, ( hdd was not working ) spent most of my time on "debug" command. Then I got a book for x86 assembly and DOS (interrupts etc). ( Which was kind of hard on non-english speaking country ) I still somehow recall some pages from memory :)
Dived into cracking/cheats, made even money on password recovery. How long those x86 knowledge carried me was unbelievable when I look back.
BioMenace and OMF worked out of the box for me but BioMenace took 8 minutes (!) to load. It would sit at the start screen (a load screen) hanging the entire time and then load really fast after the delay. Is this related to the configuration stuff you're mentioning?
This didn't occur on any other game for me, which I recall having over 50.