So what I want to know is whether or not this is that unusual for someone in real estate.

The discussion on r/politics is myopic and the discussion on /r/tax lacks detail.

From the NYT article:

The numbers show that in 1985, Mr. Trump reported losses of $46.1 million from his core businesses — largely casinos, hotels and retail space in apartment buildings. They continued to lose money every year, totaling $1.17 billion in losses for the decade.

Trump's statement/tweet:

“You always wanted to show losses for tax purposes....almost all real estate developers did – and often re-negotiate with banks, it was sport,

Now my very limited understanding of real estate and taxes is this:

• You can depreciate the building but not the land
• Depreciation can be carried over multiple years
• When you sell property you can roll those proceeds into the purchase of another property, thus delaying income tax

Are those accurate? If so, do they explain Trump's taxes?

I'm thinking not (I suspect Russian money laundering is the real source of income). However, I have yet to read a good discussion of the specifics. Has anyone read such a discussion or have insight to add?

Main story from NYT:
https://www.nytimes.com/interactive/2019/05/07/us/politics/donald-trump-taxes.html?action=click&module=Top%20Stories&pgtype=Homepage

CNBC's article about Trump's response:
https://www.cnbc.com/2019/05/08/trump-defends-tax-tactics-after-nyt-story-says-he-racked-up-more-than-1-billion-in-losses-it-was-sport.html

EDIT: As an aside, I got into a wee bit of trouble because my wife's (very) small business lost money three years running. The accountant that I worked with informed me that if a business losses $ three years in a row, the IRS considers it a "hobby" and you can't subtract those losses from your personal taxes. Is that in play with Trump at all? If not, why not?

EDIT2: I'm going to answer my own question I think. I heard a good segment on NPR yesterday that addressed my question. You can read the transcript here: https://www.npr.org/2019/05/08/721552462/president-trump-defends-himself-against-report-he-did-not-pay-taxes-for-8-years

The bottom line is it's not so unusual but it doesn't exclude the possibility of him running his businesses poorly either. So I think it's not really what the headlines have made it out to be.