I go back to the early 1970s; teletypes, dumb terminals and acoustic couplers myself.

I have to say that my worst computer experience ever was early '90s. I had some 'make or break' artwork to do - with CorelDraw 2 on a 386 DX running Windows 3.1 - by 11.30am next day, and didn't get started until 9.00pm. At this point my 40Mb Western Digital HD broke. I managed to get a friend who owned a computer parts store to go back to work and sell me a new HD, and by 10pm I was ready to re-install DOS 5 and Windows 3.1, but they were upgrades from previous versions so...

First I had to install DOS 3.3, which was on 3 x 5.25" disks and would only install from A: that meant swapping the floppy drives, then swapping back again to install DOS 4.2 (ISTR 3 x 3.5" disks) then DOS 5, Windows 3 (11 x 3.5") and finally Windows 3.1 (15? x 3.5") followed by CorelDraw 2 (another 12 x 3.5"). Unfortunately I'd forgotten the DOS 5.1 that followed the Stacker vs MS court case and so couldn't read any of the compressed floppies that I kept my work on, and 5.1 had to be installed before Windows so it was back to square one. Finally got it all running again about 9.30am.

Oh yes, those were the days!