I think America is less likely to want to buy what he's selling. Plus there will be some backlash and he's got financial interests in Russia and other countries that he can no longer "objectively' manage once he takes office since it will be a clear conflict of interest. He can't be in business when he's supposed to be leading.
Trump knew that when he took a position in public service, that it would pay far less than he makes being a real estate mogul. But he knew this when he decided to run for President. Trump will not be able to advance his business interests anymore or draw his own salary, so it will hurt him financially.
Trump will not suffer financial losses due to his presidential win. This is because this protests will come to an end and the country will run smoothly thereafter. It is just a matter of time since this will not take forever. The protesters will no longer block the entrance to the Trump Towers and hence his finances will be regained.
Trump will only suffer while he's in the White House. While he is president he can't make any money but any money that he would make gets put in a trust along with all his previous assets and so when he gets out he'll be set for life. That's pretty good for someone who just lost one of his biggest towers.