I absolutely loved reading everyone's recollections!
I had read about Indy 500: The Simulation in Car & Driver back when it came out, but since I didn't have a PC, realistic racing was a pipe dream. I did spend extensive time on Bill Elliott's NASCAR Challenge on the NES and the few times I got to play the PC version on my half-cousin's Tandy.
While back-to-school shopping at our nearest mall (a 30 minute drive from home) for my Junior year in high school, I saw a Computer Gaming World magazine issue with Jeff Gordon's car on the cover. I never liked Gordon, but the prospect of a realistic NASCAR game had me immediately thumbing through it. The article told of the same company who made IndyCar Racing, Papyrus, working on a NASCAR game. I purchases it and would read it when I was at school, or home, daydreaming of its existence.
I recall some NASCAR TV shows featuring the game, and more about it was being heard in circles in '95. That Summer ('95), my best friend got a Packard Bell PC and the game. I would go over to his house and play it, blown away by its realism, even though driving with a keyboard. He had AOL, so we downloaded the latest carsets off IWCC.
Later that Summer, I took some time off chasin' the girls at the county fair to check out a demo of NASCAR Racing running at a local computer shop's booth. A few weeks later, at Food City Race Night in downtown Bristol, I got to try the game out with a wheel, as Papyrus and Kellogg's has a trailer with what could be described as one of the earliest sim setups. I REALLY had to have that game!
For my 18th birthday in February ('96), I got a computer, a Packard Bell that stayed broke half of the time. The computer was key to me with my school work, as I was completing high school and eyeing college or vocation school. I got a copy of NASCAR Racing, and my friend and I would exchange paints we'd create on floppies, dial each other up and run (we'd mostly wreck each other), and other stuff. I found a book with a CD-ROM with tips, tricks, and a cool CD with utilities, carsets, and other neat stuff. We also had a 3rd friend who loved racing complete seasons, and we'd share stuff with him too.
In April, I went back to Food City Race Night, and a local computer shop had this cheap wheel on demo, I tried it and liked it, and purchased one. It was defective, but the shop replaced it. While it was crude, it beat using a keyboard. I had also gotten Internet, and was downloading carsets from IWCC, utilities from The Pits, as well as using Paint Shop Pro and graphics with my friend's handheld scanner and the Internet. I would later add a Thrustmaster with the analog controls on the wheel, then a NASCAR Pro Wheel. That Summer, I added IndyCar Racing 2 and tinkered with IndyCars.
Papyrus helped me in my career, and I took night classes in computer repair, daytime college courses in IT, before being bitten by the teaching bug when I got a chance to teach the night computer repair classes and switched to education. In my 15 year education career, 13 of them have been spent teaching Information Technology, and I'm now teaching where it all started, thanks to NASCAR Racing and a defective Packard Bell.