"He has had a lot of financial difficulties in his life". As said by an unknown someone about Donald Trump. Isn't it all relative? What financial difficulty could he face that would wipe him out?

What has his lowest net worth ever been?  He allegedly repeatedly stiffed contractors out of money he owed them but did he ever not pay a bill because he didn't have the money? Did his kids ever go hungry or worry about where they were going to sleep that night? Was he ever unable to get medical care for his kids because he couldn't afford to do so? Did he ever go without medical care himself because he put himself last so he could take care of his family? How broke does a billionaire ever get? Does one ever get so broke he/she is penniless and on the street? Anyone know any billionaire like that? What does Donald Trump know about the lives of those living on the edge of disaster?