After several years battling disasters—both natural and man-made—at Michael Dell’s resorts in Hawaii and California, the investment fund that manages the billionaire’s personal fortune is trying to reboot his hotel empire.

MSD Capital LP, which oversees some $12 billion in assets for Mr. Dell, has brought its payments up to date on its $425 million mortgage on the Four Seasons Maui resort, likely signaling a restructuring of the loan. MSD had been delinquent for roughly 16 months on the debt after the investment manager quit covering the property’s debt-payment shortfalls early last year.