His underlying message isn’t targeted at the actively engaged electorate at all.

I can't say I agree with this. He's targeting a group of people that have grudgingly supported the Republican party in the past, and who have been totally abandoned by the Democrats: blue collar workers.

More generally, I don't really understand why so many people are confused about how Trump continues to maintain support among a certain segment of the population. I think there're two things going on here. First, for the aforementioned blue collar folks, Trump is the only politician in decades who actually acknowledges that there's a problem. He won't say what truly needs to be said, namely that those jobs are never coming back, but he's at least saying something. So I think there are plenty of people would rather roll the dice with him instead of voting for a candidate who definitely won't do anything to make their lives better.

The other thing is that we have been lied to so consistently over the past however many years that no one takes a politician's promises or platform especially seriously. We know it's an act, and for some, they'd rather just flip over the table and hope the replacement pieces are better (and worth the damage in the meantime). Finally, I think people frankly have an inflated opinion of Clinton, simply because of how scary Trump is.

I'm not going to lie, I understand. Part of me would love to see Trump win and then stomp around the government like a kaiju with ADHD. I'd be more in favor of this if I didn't think he would wreck U.S. foreign policy for decades to come. China and Russia will become much stronger players on the world stage with a Trump presidency.

Anyway, I'm getting away from your point (and mine). I think Trump is acting like he's different because he truly believes he's secretly a genius who can fix it all. His whole life has set him up to believe this; he's been almost wholly insulated from any consequences of failure. If every decision appeared to you to work out perfectly, wouldn't you think you were extraordinarily qualified?

I question the idea that Trump had that specific a plan. Maybe some of his more experienced campaign staff began to try to formulate one after he began running, but it certainly doesn't seem like he came in with one. He just decided to wing it, and that of course he'd be successful, since when has he not been?