When President Trump leaves the White House in January, he will face some of the deepest financial and legal challenges in his family business empire in decades.

No matter what he focuses on after the presidency, the businesses will require his attention. Two New York investigations will continue after he leaves office and the Trump Organization will need to avert a potential cash crunch caused by looming debt maturities at the firm’s real estate holdings. Personal guarantees Mr. Trump made on some of the organization’s debt add urgency to shoring up its financial position.

Trump Organization executives say a key focus will be growing the brand globally once Mr. Trump leaves office. Yet those plans will face hurdles. In China—a market long eyed by Mr. Trump—the president has become deeply distrusted after his trade war damaged U.S.-China relations. In Europe, some of the Trump trademarks have been eliminated by legal challenges.

The Trump Organization might soon slim down. Several properties are for sale, including its Washington hotel and two skyscrapers in New York and San Francisco that are part-owned by the Trump Organization.