> After a few years of pain, people would've gotten with the program, so to speak.

Not necessarily. This was still very much the time in which choosing to stick with an old version which worked (e.g. Windows 3.1) wasn't uncommon.

Just look at how many people jumped from XP to 7 due to the network effect of "Vista sucks" and then multiply that by the fact that, at the time of 3.1->95, people had far fewer computer security concerns, if any.