"Things should be made as simple as possible, but not one bit simpler." ~ Albert Einstein
You can still write off debt funded losses. That is not really controversial. But not paying back debt is supposed to create income (called, inventively, cancellation of debt income) that usually results in you losing the tax benefit of the loss. The latest thinking/speculation on what the tax returns show is Trump may have taken a Gitlitz position, which let him take the benefit of the loss without impairment from the CODI. That's legal, the courts said so, but philosophically wrong and was subsequently changed by legislation.
Yes. Differences of magnitude warrant different responses in all sorts of situations. For example, I'd like to think that if the 9/11 attacks had only succeeded in killing one American that our response would not have been to start wars with two countries. Or that we wouldn't consider using the same punishment for someone that shoplifts a dollar candy bar as we would someone that manages to grab a multi thousand dollar piece of jewelry at an expensive jewelry store. Or on the positive side, I will have a different opinion about one's commitment to helping people with AIDS if one has a foundation, to which they have donated millions of dollars personally, and that has bought HIV meds for half the infected people in Africa compared to another rich person who drops a check for $25 in the mail to GMHC.
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