> Several of Trump's corporations have been bankrupt 4 times...
FTFY.
> relies heavily on debt to finance his real estate ventures
Real estate has high start-up costs but holds lots of value. Debt is the perfect vehicle to finance real estate, ever wonder why most people take out mortgages to buy homes, but give up equity to fund tech start-ups? You use the investment vehicle that makes sense for the type of business.
> It's well documented that he took on hundreds of millions of debt in the form of "junk bonds" (so called because of the high risk of default and the resulting high interest rate - 14%) in order to pay for his casinos in Atlantic city, for example.
Of course, casinos are high risk. Bond rates depend on risk. Also, most business debt requires a higher rate than say, sovereign debt.
> it appears at least one of his properties in NY has been modestly successful in recent years - but that property had well below $5 million in profit in 2014 and was losing money before that.
And? With real estate you don't need profit, you just need to build equity.
Tl;dr: Real estate isn't like other businesses, it has its own set of rules, accounting and financial practices, etc... Just like tech companies are different from factories which are different from restaurants, real estate is (gasp) different...