For old games, maybe you should look into DOSBox.
Win98, W2000.....15 yrs old vs 13 yrs old. Both long discontinued. I still have a working Win2000 install. An old laptop, turned on maybe once or twice a year. Just to connect to the car and run diagnostics. When that finally dies, I'd not pay actual money to buy another Win2000 install to try to reproduce it. I'd move on with newer equipment.