Trump is not a self made billionaire. He inherited a vast fortune from his father, and was skillful enough to grow that fortune to what it is today. It is also widely believed that he has hugely overstated his personal wealth.
As well as all of his business success, there have been many business failures (just have a look at Trump University for instance), in these cases he has taken many average working Americans for a lot of their hard earned.
Yes the Trump name appears on a lot of buildings and resorts, but that doesn't mean he owns them, or even has anything to do with them. In many cases he is simply the naming rights holder (much in the same way that Etihad Airways doesn't own Melbourne's Docklands Stadium, they are a naming rights holder). This works as a cozy relationship between the actual owner/ operator and Trump. They get to bolster their credibility, while he gets to spread his apparant empire. Perfectly legal, although slightly missleading.
Going on his own comments in just this Presidential campain, Trump is either a massive liar, or a massive racist and bigot. The truth is probably a bit of both.
He has suggested all Mexicans illegally living in the USA are rapists and criminals. That is a racist statement.
He has said he will deny ALL muslims entry into the USA. That is a racist policy
He has suggested he would endorse the torture of suspected terrorists, and the killing of their families. That is an international war crime.
Do I think Trump is the next Hitler? No.
Do I think Trump is a lying bigot? Yes.
Americans surely can not be this dumb.