1) Reader Rabbit on an Apple IIGS in the late 80s. I might've been in Kindergarten. Found the boxes stored in an unreachable storage area at my dad's house recently. Knowing how he took care of things, it probably still works. He won't let me touch it.

2) Fast forward to early middle school, Ultima VII on an NEC desktop, 90s. That game was great but also a pain in the ass. Had to make a startup floppy disk to help with memory allocation and something else. Learned DOS things. For some reason the disk wouldn't work from one day to the next so would have to reconfigure it frequently. Also learned the hard way not to fork too much with autoexec.bat during this period.