Dang,
I missed this QOTD, but hope it's not too late to comment.
My first computer "experience" was in a local electronics factory, where the owner had built a machine from a kit and played "Adventur", the precursor to the Zork game series. It was a text based adventure, and it was amazing to me. Some time later, the guy who brought me to that place purchased a VIC-20. He had no clue how to use it, so I "borrowed" it for a couple of months. Then I got my first machine, a Commodore 64, and eventually got all the bells and whistles for it (still have it).
My first "real" computer was a 80286-12, and with a dot matrix printer, cost me $2000 at a computer show. It eventually sported Windows 286! My kids grew up with Dr. Halo (aka Paint), and the other early programs. I kept the computer in the attic, and after my first heart attack, I lacked the ability to tell when the room was too hot. The disk drive fried, and the old tech was no longer available. I replaced the custom machine with a bare bones 386-16, and eventually built a 486 DX-100 in the old 286 case.