And again I think the problem is Trump supporters understand that and did not elect Trump to (or at least in the actual hope that he would) "make things better."
When you put a bag of flaming dog poop on your ex's doorstep, it's not in the hope that it's going to make them get back together with you.
Trump is, in every way, a bag of flaming dog poop.
He wasn't elected to fix anything and people keep missing the point variously either scratching their heads in confusion or waving their arms in frustration about how Trump isn't fixing any of the problems his supporters are (either genuinely or ostensibly) angry about.
The fact that Trump isn't making anything better is not hurting him. Because he wasn't elected to make things better. He was elected to hurt/confuse/rile up/get back at/troll this vague, poorly defined, mythical "Elite out of touch liberal intellectuals" that Trump's base was told caused it all.
You said it yourself, Trump is unprecedented. Because he is, I honestly believe, the first President ever elected specifically to break the system.
That's why I still say he's winning. Everything he's done wrong is the point.