Reading the detailed breakdown, the only things he's done or invested in that have not lost money are two early properties he was forced out of but left a small stake in, and his reality TV appearances. Everything else has lost money.
To add to this: Trump International Hotel (the one in DC) was put on the market in Oct. 2019 for $500M. There were no buyers before the sale offering was canceled due to coivd-19.
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.