Re: Look it's really quite simple.
"I sometimes wonder about the way people get really anxious like the second an OS drops out of mainstream support"
It's because of marketing. OS and some software vendors really need you to keep updating, and they're very quick to jump on "security" as the stick to beat you into doing it.
Note: I'm not saying that the argument is invalid, I'm saying that it's greatly exaggerated. Also, it's not really that hard to run an outdated OS or other software in a way that is about as secure as if you're up to date. It just requires a bit of care and attention (which people should be engaging in anyway).