I think the point is that no major US Company has filed Ch. 11 more times in the last 30 years than Trump's. The fact that he didn't file them individually is a silly, silly argument (akin to "But President Obama has accumulated $0 of the US debt personally). If anything, it's more troubling to me for what should be obvious reasons.
But make no mistake, I fully understand your position. Which is why I pointed out the hypocrisy works both ways.
As for your last question, I have no good answer. I've wondered the exact same thing.