The biggest thing I remember, vividly, was setting yp the autoexec.bat and config.sys manually. I'll never forget 220/5/1. Trying to get 600k of base memory was a challenge. Enter himem.sys and the loadhigh= statement. It really got interesting with mscdex.exe when the cd rom interface was a propriatary one on the sound card as opposed to a standard ide interface. I had a Gateway 486-66 with a mitsumi cd-rom like that. We would run WFW 3.11 but had bootable floppies to boot into MS-DOS for gaming so we had enough available base memory. Popular games for me were Indycar Racing II by Papyrus and Descent by Interplay. I launched Descent a few months ago on a DOS machine I threw together and the graphics were so bad it was hilarious. Made me wonder how I ever flew through all those mine shafts.
Papyrus came out with a special edition of ICRII that used a Rendition video card that really set the standard for graphics. After that, the Voodoo cards followed and I moved on to the first Tomb Raider. The graphics were stunning. I can still see Laura in all her glory.
My friend and I would use 28,800 modems and direct dial connections and play ICRII for hours, while speaking on the speaker phones, no Ventrilo or in-game chat in those days.
Sorry, got a little off track reminiscing there.
John