Uh, where are the Maxis games in the OP? Simcity, Sim Ant, Sim Earth, c'mon!
I'll never forget trying to upgrade the family computer from Windows 3.1 to Windows 95, with out really asking or informing anyone in the house. I spent some birthday money on a neat looking PC game called Free Enterprise, with out knowing it required Windows 95. I also really wanted to install AOL 3.0 which also required 95. I mentioned this to my aunt, to which she said "well just take these disks and install it!" Happy as a clam, as soon as we got home, I popped in disk 1 and got started.
Being a know it all 12 year old, I didn't bother with any backups, didn't check the integrity of the disks, just booted to DOS and popped in the first disk.
There was like 15 floppy disks, maybe more, but somewhere in the middle I ran into a corrupt disk. Totally botched the computer because we didn't have a Windows 3.1 copy laying around, the computer was given to us by my grandpa, and I couldn't muster the courage to tell him what I did.
I ended up getting very proficient in DOS and was super thankful my grandpa installed PC Tools. The upside was this allowed me to delete Windows 3.1 completely and I could install more games. We had a tiny hard drive so I ended up not really missing Windows.
Another "fond" memory of 90's PC gaming is desperately trying for weeks to get Warcraft II working. It required certain amount of RAM, I knew the PC had the amount of RAM required, but it wouldn't work. It took week or two of me digging through "How to use MS-DOS" type VHS videos and reading manuals, to finally learn that I could allocate RAM by editing autoexec.bat.
The glee that I had when that Blizzard intro popped up.
Not long after that my dad bought us (me) a Gateway 2000. It had a Pentium II 233MHz, 32 MB RAM, and a Riva 128 4MB. The jump from the 33Mhz 486DX was huge. It also got me back on the internet which I really missed.
Wow, nice throw back to that era's web design. I had a Voodoo 5 (got it for free after 3dfx went under) and remember having to obtain various drivers for that thing very well.