My "holy shit, we're in for... interesting times, and like, soon" moment was when Trump suggested his supporters might shoot Hillary if she won ("If she wins, I can't do anything about it. But the 'Second Amendment people'...."), and didn't see a huge hit to his popularity, and supporters in his own camp distancing themselves, immediately.

Norms are dead, you can just suggest assassination of your opponent and still win a Presidential election now, the batshit crazy stuff's not just for races in rural Montana or whatever. Like, IDK how this reads to younger folks, but I assure them that things are now happening practically daily that would have been unthinkable 15 years ago, let alone farther back. Things got visibly weirder fast.