John Paulson made a fortune on Wall Street betting the housing market would collapse. His reinvention as a property tycoon opening Puerto Rico to the wealthy is proving trickier.

The 67-year-old has spent hundreds of millions of dollars over a decade buying and developing luxury resorts, condos and high-rise offices in the U.S. territory. The island’s government has introduced tax breaks to attract rich home buyers and businesses, and Paulson has said the opportunity is akin to Miami before its epic boom in the 1980s.