Our reporters explore all this and more in this week's "Inside Politics" forecast, where you get tomorrow's headlines today.
Donald Trump wears many labels: real estate mogul, reality show star and now, Republican presidential nominee. So how does an opponent take on Trump when his appeal goes beyond politics?
The Clinton campaign may have an answer.
Clinton's camp believes it's starting to see results from its attacks on Trump's business record -- especially the not-made-in-America jab when it comes to Trump-branded products.
CNN's MJ Lee says new Bloomberg Politics polling finds 61% of likely voters are less impressed with Trump's business expertise now, compared to the start of the primary campaign. And if Clinton's messaging is working, Lee says her campaign will really be driving it home in swing states:
"The Clinton campaign has been very relentless in going after Donald Trump post-convention, especially in going after his business practices like his ties made in Bangladesh. That was an ad that I saw in Nevada over the weekend. And if you look at her schedule in the coming weeks, she is going to Pennsylvania with Vice President Joe Biden and then Ohio. These are places where they especially want that kind of message to stick."
2) Seeing red in blue NY
Nothing in 2016 has been business as usual, so why should the electoral map? At least that's what Trump is hoping.
He's said time and time again that he wants different states in play than the ones the GOP has traditionally targeted. That includes his traditionally Democratic-leaning home state of New York, which he vows to make a swing state.
Time Warner political host Errol Louis examines Trump's reasoning for his New York state of mind:
"Conventional wisdom dictates New York is out of reach. Don't bother. On the other hand, down the ballot, at least half a dozen congressional seats in New York are actually in play. So this is not something that the RNC is going to write off. It's a question of whether or not Donald Trump and the RNC can get on the same page, truly, and try to put New York in play both for the congressional candidates and for the Trump campaign."
3) Trump's ground-game problems
Team Trump has spent zero dollars when it comes to general election TV advertising. Trump has said he hasn't needed to because of his media exposure. But the Trump camp says it'll start buying ad space "soon" to woo voters via the airwaves.
But beyond ads, what will Trump spend his latest fund-raising haul
CNN's Phil Mattingly spoke with GOP sources who say the cash is going toward the campaign's ground game. Mattingly explains how that money may only go so far when it comes to targeting voters:
"Donald Trump didn't have a data operation in the primary. It was unheard of. The RNC does have a data operation. They spent more than 100 million dollars building that over the course of the last four years. So, Donald Trump is just going to take the RNC data operation. Makes sense, right?
"Except for that data operation was built for a very generic GOP voter set. A voter that Donald Trump doesn't necessarily need if he wants to win. He wants GOP voters who are not traditional. Marrying those two groups is extraordinarily difficult. The campaigns are putting a lot of effort into that."
4) That 'Dump Trump' talk
It's no secret that some Republicans are worried about the "Trump Effect" when it comes to the faltering candidate's drag on down-ballot races. But that doesn't mean they're just going to ditch their candidate as November nears.
Why? Because there's uneasiness about when to make that move, if at all, and the precedent behind it.
New York Times' Maggie Haberman says look no further than 1996 to read the 2016 tea leaves:
"Everybody talks about the Bob Dole year, 1996 ... Bob Dole was a different case. He was friends with the then-RNC chairman, Haley Barbour and he himself was a senator. He had a different view of this.... That is not what you're going to see this time, if you see it.
"The RNC is also still pretty dependent on Donald Trump, in terms of fund-raising. And it is not clear exactly how that will work out once there is a split. The resources are linked together in a different way than they were in that year when there was still soft money."