OWNERSHIP & TRAVEL Page 23 Jul / Aug, 2026 | TimeSharing Today
mitment and execution matters deeply to a board that spent nearly a decade in litigation and who has experienced the impact of making the wrong choice.
“ We could have very easily found ourselves on a path to dissolution,” Osterman reflects.“ I believe within a year we could have lost the resort if we’ d chosen the wrong company.”
A Resort, Still Standing
Today, Outrigger Beach Club is financially healthy. The maintenance fees have remained historically low. The first increase in five years, a modest 3 %, was recently approved. The ownership base engagement has increased. The property is ADA-compliant, family-friendly, and, as Osterman notes, thoughtfully designed for guests with mobility considerations- including a family member, who navigates the resort without difficulty.
His son Jay, who first visited as a sixmonth-old in 1987, is now 38. He recently brought his own son to Ormond Beach. Three generations have passed through the resort, enjoying the same strolls along the sandy beach and sunrise view from every window.
Jay, Bryant and Tina.
“ It gives us a great anchor point for connection,” Osterman says.“ Life evolves, circumstances change, but the resort remains constant. That continuity, that family legacy, is an incredible part of this equation.”
For board members weighing their own management decisions, whether in the calm of routine operations or under the pressure of transition, Osterman’ s story offers something more useful than
a formula. It offers a model: stay curious, do the work, protect the things that matter, and don’ t settle for common, generic answers to complex questions.
The ocean has its own rhythms. So do well-run resorts. The key is knowing the difference between a wave that will pass and one that will take everything with it, and having the right people beside you when it comes.
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