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You can take a look at their financials. Compare their reserve fund to other, similar resorts. Have there been special assessments in the past? Having MFs extremely lower than similar resorts is another indicator. If the property is managed by a company that manages other properties, do they have a history of special assessments? Look at the physical property -- is it out-of-date and in need of general repair?
See if the HOA puts a lifetime on elements of the resort (Roofs, Paving, Elevators, Painting, Appliances, Furnishings ...) and adds a reserve in the MF to cover those items.
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