Windows 3.1 and 16 bit would be a little too painful for me. Windows 95 was quite nice with 32 bit and preemptive multitasking though. I kind of miss this or Windows 2000.
NT4 was very nice, although no USB. Didn't crash and was smooth as butter.
Initially turned out that it had been set to RS485 mode, and I didn't have an adapter, and I didn't even know if it worked if I was able to get it into that mode. So with the help of a sympathetic engineer at SICK, he had me send to unit to them and he reset it (to RS232) and tested it. When I got it back, I tested it with the machine again and it worked perfectly. He didn't charge me anything for the service.
You don't see that kind of support anymore - almost no company will say "yeah, sure, send us a unit you bought second-hand off Ebay to us and we'll take a look at it, fix it, etc - and no charge to you, either - even though you're just a hobbyist and have no support contract" - it shocked me.