That said, if Trump broke the rules to arrive at those losses, fines and/or jail would be appropriate, depending on the severity of the violations.
Ah, the old "if true..." tactic.
There are IRS agents who dream of nailing a billionaire. It's what they live for. If Trump broke the rules to arrive at those losses, we'd know about it. If Trump took any deductions that the IRS allowed, then those deductions are allowed. If they aren't allowed, the IRS disallows them, but no one goes to jail for having deductions disallowed.
As for the haircut deductions the media is (utterly disingeniously) hyperventilating over, that was an employee expense paid by Trump's business rather than the production company.
If your read deep into the Times piece, they admit that he paid a lot in taxes and didn't take any deductions that he wasn't entitled to take. Those two years where they claimed he owed $750, Trump actually overpaid those years by millions, and told the IRS to hang onto it for future tax liabilities. The $72 million refund that he got to offset earlier losses, that came about because of an Obama era change in the tax code that allowed earlier losses to be written off.
The terrifying $300 million loan that is coming due, that Trump personally guaranteed, that somehow makes him a national security risk for bribery, is nonsense. The correct response to Trump having a $300 million dollar loan coming due is, "So?"
Large corporations have loans like that coming due every month. It's routine. If you have enough assets, or cash, or, more importantly, cash flow, to service the loan, that's all the banks care about. The one thing the media won't report on is Trump's cash flow, because that's the most important factor in large loans like that, and Trump's cash flow is in the billions according to the fake news own public reporting.