I think Trump will go to the lowest of low, I think what he said about Megan Kelly and her period shows how low he will go. If Trump attacks Hillary on stage at a debate, it will make him look even more like a bully, since he is so tall, and larger than her, I think it will work against him, especially if its about personal things.
Wall or fence?
Is the issue that we’re building a barrier on the border, or whether the barrier is a wall or a fence? A fence would be fine but a wall isn’t cool?
Yeah, who cares about accuracy or truth? I still think Our Candidate will show her strength & Your Candidate will act a fool…
But does being skeezy and corrupt turn one into a politician?
That’ where Clinton’s weakness lies. She’s flip flopped on more than any politician in history to fend off the Sanders challenge. No one is going to care about the distinction between a fence and a wall. And since she’s made a strategic decision to promise Latino voters every single item on their wishlist, it’s not like she supports the fence anymore either.
You’re failing to take into account that “any politician in history” is a category that includes Romney.
Clinton seemingly has a history of changing her views based on what polls well, but Trump speaks out of both sides of his mouth simultaneously. He’s pro-life and pro-choice. He loves Mexicans, but they’re criminals and rapists. He loves China, but they’re destroying our economy. He favors universal health care but will undo the ACA… He needs to be really careful if he’s going to try to paint her as a flip-flopper.
On the other hand, she just has to point out that his big proposals are even more unrealistic than Bernie Sanders’. We can’t afford the $25-30 billion dollar wall he is proposing. He can’t make Mexico pay for it. Even under his direct order, the military is not going to start dropping bombs on terrorists’ families. His suggestions a that we expand our use of torture but restrict free speech by the press are going to appall voters who haven’t yet been paying attention to what he’s saying.
I really, strongly dislike Clinton. But she’s a decent debater and will make him look silly. His best move would be to refuse to debate her at all, just like he decided to skip some of the primary debates. He’s got nothing to win.
You haven’t been listening to the Hamilton soundtrack, have you? Its really hard to beat Aaron Burr for flip flopping (plus getting accused of treason, and killing the former Secretary of the Treasury.) 
A debate with these two will be the ultimate in what the DoD calls “asymmetric warfare.” IOW, exactly what works best for one side fails miserably for the other. Which essentially means that the side which determines the ground they fight on determines who wins.
Had Hillary been an R, she’d have been Fiorina’ed in the early R debates. Her policy-centric message would have been lost in the laugh track of the others’ frat-boy repartee. (I originally typo-ed that as “fart-boy”, and almost left it; it works good either way :))
Had Trump been a D and participated in the Clinton / Sanders debates he would have been tongue-tied. Unless he was able to wrest the mike away from the mods and turn it into an ego contest. Which I think he would have.
My bottom line: No matter how it actually goes, the Trump fans will see their champ winning hands down. And the Clinton fans will decry Trump’s absolute lack of policy meat as proof of his abject loss.
TV is a mostly emotional medium. Trump plays an emotional role. Clinton plays an intellectual role.
When each side as their own scorecard there will be no objective way to decide who “won”. But IMO most of the noise will be about Trump continuing his brash bullying way unstoppably towards the White House.
I wonder whether Trump will try attacking Clinton from the left on economic issues.
Look, nobody has done more to raise wages than me. I built a casino in Atlantic City and I paid the workers there an excellent wage. Now Hillary over here, she’s only promising to raise the minimum wage to ten dollars an hour. Well that’s a minimum wage for losers! When I’m President, we’re going to have the most big, beautiful minimum wage that the world has ever seen. We’re going to take the minimum wage to twenty-five dollars an hour. And we’re going to give every worker a free pony.
And what has Hillary ever done to help labor unions? Nothing, that’s what! She was First Lady, she was a Senator, she was Secretary of State, and in all that time, unions just kept getting smaller and smaller. But I love labor unions, and unions love me. And When I’m President, I’m going to appoint a whole bunch of excellent people to the Department of Labor and we’re going to make unions great again!
How about Trump promising to mail every American a check for, oh, say, $1,000? Maybe he’s holding off on that kind of legalized bribery, in the primaries, so it can be an October surprise.
The honest, and unpopular, response would be that this is bad economic policy during an expansion.
I’m reading a biography of Huey Long, often considered another demagogue, who was assassinated before he could go far in running against FDR. A famous Long quote:
http://www.bloggingthebookshelf.com/2012/09/03/of-roosevelt-long-said-scornfully-i-can-take/
Between Bill, and Hillary’s not entirely missing conscience, Trump can outpromise her. I think she’ll win anyway, but it’s a problem.
Trump has already gone there, in a vague way.
I’m really wondering whether Trump will bring up Juanita Broaddrick’s allegations at some point. If he set it up correctly, he might be able to put Hillary in a bind of sorts, as she would have to say that Broaddrick’s allegations are lies, though many of her allies have been pushing the idea that all women who make rape accusations have a right to be believed. Some sources are already noting the tension, but if Trump were to bring it up in a debate, everyone would be talking about it.
The thing is that Trump has already plainly gone back on his word so much that no one but the sheeple will buy that he’d keep it, whatever he promises.
Trump can go after her all she wants - it will only backfire. Winning a debate in the eyes of bitter middle-aged and bigoted white males is one thing; winning a cross-section of the American electorate, which is required to win a general election, is quite another. That’s what Trump’s loyalists don’t understand now, but what his detractors in his own party know all too well, and that’s why they’re terrified if he makes it to the 1237 delegate mark.
For the record I’m not saying that all of Trump supporters are bigoted or mean-spirited but it does seem to be a dark energy that’s driving his campaign. You could probably point out dark forces behind a lot of campaigns. I’m not trying to ruffle feathers, but I do think that if Trump wins the nomination (and I’m not even so sure of that right now), his tactics will not work at all.
Being nasty would backfire. If, on the other hand, surprises everybody and starts sounding a little nicer and more gentlemanly, that might actually attract some of Clinton’s supporters. And then - and only then - could he hammer away at her voting record on things like NAFTA. But his negatives with female voters are at near historic lows in modern times. He will have to rehab his image a lot. And that’s saying nothing of his comments toward Hispanics and Muslims, and the footage of his campaign and supporters roughing up black protesters.
And how do you think women will react to attacks on Clinton? I just read in the Times that only 50% of women who identify as Republicans can imagine voting for him. My guess is that some will sit it out and others will support Clinton. How can he win an election that way?
Ah. I had not thought of that. Some may be drawn to vote for her.
And the 2016 Presidential race turns into a dick measuring contest…
“It’s YUUUUUUUGE!”
Sorry, I couldn’t resist. 
Dude, you do remember that you’ve said both that you are pro-Clinton and anti-Trump, right? Sure, she’s not your favorite, but she’s the closest to what you want, right?