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.

In the US the tax rate on the bottom 78% of earners taxes was less than 7%

England has a tax rate for the same income of 11.5%

The top 6% (Avg Adjusted Gross income 514,000) paid $840 Billion of the income taxes

The Bottom 49.1% (Earning less than 45k AGI) paid $97 Billion of taxes, but 27.4 Million Households filled for $66.7 Billion in EIC tax credits

If the taxes on the bottom 78 percent were increased 6% to a level similar to England the USA could have universal health care

The US Spends 3.4 Trillion on Healthcare.

Just 5% of Americans Account for 50% of U.S. Health Care Spending. So taking away the top 5% means the US spends about 5,500 per person. More than UK, but with a long term approach we can tackle that.

1. Saying no to covering all issues. See above. Total cost down to 1.8T

2. Accepting a tax increase

• Doubling the Medicare withholding will provide 500B
• Down to 1.3T

1. Reallocate state spending In 2015, state governments across the country spent a combined $605 billion on health care

• Down to 700 Billion

1. Increase taxes 6% across the board, like those of countries that provide healthcare. 600B in Funding

• Down to 100 Billion

1. 1/3 of expenses in 2017 was payable for hospital room rentals and 21% was to doctor's office billable hours

• Increase utilization to make hospitals & Doctors more efficient so cost can be cut
• 1% reduction in billable hours and room rates Down 100B
• Adjust pricing based on cost savings
• Repeat

If the US had higher taxes for gas we could have a better Infastructure. Using rough math we in 2017 underfunded the highway dept about $21.5 billion

• 40 Cents per Gallon vs 18.4 cents currently
• 33 Cents vs 17.5 cents for Highway maintenance at fully funded for at least the next 5 years
  * 1 Cent vs 0.9 cents Gas Safety and storage. Round it up to a full penny better saftey funds for better clean up
  * 4 cents a new Green energy tax for Green projects
• 2 Cent New Metro Projects tax

$5.5 Billion annual funding for projects, plus using funding not going to covering the underfunded highway dept means who doesn't want to announce a 10 year $250 Billion Green Deal Project. Get States to match it 40/60 and its a $600 Billion Project

$96 a person more and With this Major Cities can tackle major projects and Rural cities can apply for the Metro Funding. $1.5 Billion each state gets on average can be applied however but that's encouraging moving to a Green plan.

The U.S. combined gas tax rate (State + Federal) is According to data from the OECD, is the second lowest (Mexico is the only country without a gas tax).

The average gas tax rate among the 34 advanced economies is $2.62 per gallon. In fact, the U.S.’s gas tax a rate less than half of that of the next highest country, Canada, which has a rate of $1.25 per gallon.

We want to have the European advanced economy of our peers but we arent wanting to pay for it