Real estate can frequently show a tax loss from depreciation while generating cash flow. But depreciation only applies to improvements, and it sounds like the golf courses are a significant part of the losses. I don't know enough about golf courses to determine if depreciation is a big factor here.
So this is negative cashflow, not counting depreciation.
Unless those had some type of synergy that made his other properties and brand more valuable overall, those sound like poor investments.
You don't put a marquee property on the market if it is making money. Especially the one in DC. Especially while you are the current US president.
https://www.wsj.com/articles/trump-organization-exploring-sa...
My business also shoes a tax loss almost every year - that's just normal good money management.
Amazon showed a tax loss literally every year ever.