“ Some places become more than destinations. They become traditions.”
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was stepping back, and the board needed to find a replacement.
Osterman treated the search the way he’ d learned to treat complex vendor decisions in automotive engineering: rigorously, systematically, and with full documentation.
He built a request for proposal from scratch, refining it with the board until it reflected the resort’ s vision- which was unambiguous: preserve individual, deeded-week ownership; resist corporate drift; keep the property affordable, familyoriented, and sustainable for the long term. He identified seven management companies, vetted them down to three, sent out the RFPs, and organized onsite visits and structured interviews with each finalist.
He also built a scoring template- a tool that allowed each volunteer board member to independently assess and document their impressions of the three candidates. It was an engineering process applied to a hospitality-focused decision.
“ During the due diligence process, we looked at everything,” Osterman says.“ Better Business Bureau information, legal dockets, open litigation found on
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“ Some places become more than destinations. They become traditions.”
public records, Google reviews, Facebook groups. I even used AI tools to help scrub available information. Legal counsel is a heavy component of the process, but it can’ t be the only lens. You need a multipronged approach.”
One of the three finalists was Lemonjuice Solutions. When the board reconvened to vote, the corporate trustee abstaining, the four individual-owner members reached a unanimous decision. Lemonjuice was awarded the contract, effective December 1, 2025.
What Mattered Most When Osterman describes what differentiated Lemonjuice in the evaluation,
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he’ s specific. It wasn’ t just what the company said- it was the breadth and credibility of what they could deliver.
Other companies, he explains, offered essentially a single answer to every hard question:“ If you have problems, we’ ll buy your weeks.” That kind of solution dissolves the very thing the board was trying to protect.
Lemonjuice, by contrast, came to the table with multiple tools- experience supporting legacy interval ownership and the track record to prove it, the technological infrastructure to actively market unused weeks and generate revenue, and the capacity to manage a transition intelligently if needed. That last capability wasn’ t a concession to pessimism. It was evidence of sophistication.
“ The comfort level we had with Lemonjuice,” Osterman says,“ is that they had the ability to manage transition should that need to happen and to give us the best chance at sustainability for the long term, whatever form that takes.”
Since the transition began, he’ s watched them act in accordance with what they promised. The alignment between com-
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