Don't... don't frame your arguments in green text ever again. That's not a good thing to do. 

-Getting a million dollars and then being smart enough to invest it isn't amazing. Sure, I'm not saying the guy is an incompetent dweeb. Just because he might have some vaguely pertinent skills, and because he wants to do well, doesn't mean he will. This is what I personally take from Trump; I think that he started with an easy task (to make money in NYC with one million dollars), that he did completley own that task, and that a big part of why he has done so is because he is a marketing genius, and his product is himself. He knows how to make an image - that is his skill. But, considering that he's never faced real hardship, considering that he has been in the spotlight for so long, I honestly think he is somewhat eaten up with that ego. There is the problem. Though he is no doubt hamming it up for the crowd because that's how his marketing system works, I think he believes himself to be at least partly as great as he says. In which case, his intentions don't matter. Nobody intends to enter the white house and fail. It's not like GWB just didn't give a shit. No, they fail because they don't have what it takes. And I don't think Trump has what it takes. Like GWB, his advisers will hold up his presidency, and we will be at their whim.

-Putin comes up because Putin's goals for Russia and America's goals for the world don't mesh. If Russia could be handled by a quick handshake and a wink, it would have been done already. I'm not saying that Putin will win arguments. I'm saying that Putin will play Trump like a fiddle. This is because, like I said, I think Trump has somewhat convinced himself that his charisma is genuine, and that he is at least partially as great as he says.

-Good. Trump found a base. So has Cruz, Hillary, Bernie, and even Rand Paul. That's not impressive.

-This is still an offensive comparison. Washington and Lincoln weren't daring mavericks going against the media. They were humble, contemplative men who at no point could ever be imagined talking about how great they were. Trump hasn't done anything do touch their legacies. Just pushing a grand plan doesn't make you a great person. Hitler did that. Stalin did that. Jim Jones did that. A good leader isn't just an unpopular guy that people listen to.

-He has friends because he has money. Yes, a person can loudmouth their way into connections if their methods make them powerful to schmooze in the right circles. That somebody has friends isn't particularly impressive as far as arguments go anyway. 

-He's popular with the lower classes for all the reasons you are implying, not for the reasons you are saying. Everybody, if they have even an ounce of humanity, secretly dreams of throwing molotovs at something they perceive as more powerful than them. It's a big part of both the Trump and the Sander's campaign - anger at an establishment they feel no longer represents them in the slightest. Xenophobia is the oldest political trope in the book. I don't think Trump is xenophobic so much as he is using xenophobia to get to power. And don't fall for the tumblr invention that xenophobia or racism is something only white people do. Everybody wants somebody to be better than, especially at a time when most of us are at least vaguely aware that our circumstances are going to get worse. Illegal immigrants are an easy target because A: They are different, both culturally and linguistically, and B: They violated a law, which makes it easy to justify hating them. The border situation definitely needs to be attended to, but it isn't the zeitgeist issue of our time. That he is focusing on an easy votes issue instead of on real ones exactly shows that he isn't a serious candidate. He's the candidate the Republicans deserve, but not the one that they need.

As for the entire media thing... that's so sad. It really is. The Media is another industry out of dozens that treat their mission too flippantly because doing so makes them money. This idea that our nation's only corrupt industry is the media is peculiar. And it doesn't matter, because you're completely wrong about their opinion in this matter anyway. The media love trump. They absolutely adore him. He's the best love-to-hate story they've been able to sell in decades. That's why they talk about him all the time. As a basic rule, if you want to find the person the media hates, find the person they aren't talking about. Everything else is marketing.