Comment My first Windows machine (Score 1) 387
I did an internship at a telecom research facility around that time. They provided me with a 286 outfitted to run electronics simulations software. It had 2 MB RAM installed on an ISA card (or a predecessor thereof, it's a long time ago). It ran Windows 3.0, sort of. 2 MB was too little, and the thing crashed constantly. Combine that with the clumsy UI (File Manager and Program Manager, for instance) and the mess of applications that hadn't standardized yet (every program used different shortcuts), and the experience was less than stellar.
The contrast with my own Macintosh was huge. If you think us Maccies are smug now, you should have seen us then.