Start with the use calendar
How many nights will the family actually use the property? Which seasons matter? Does the location reduce friction enough to increase use? A premium for direct resort access can be rational if it materially changes the family experience.
Calculate carrying cost independently from appreciation
Taxes, insurance, HOA or club obligations, staffing, snow, landscaping, utilities, repairs and periodic capital projects should be visible before any appreciation assumption is added.
Understand what makes the property rare
Rarity can come from location, acreage, views, ski access, architecture, privacy or a combination. The stronger the uniqueness, the harder it can be to find truly comparable sales.
Rarity can also narrow the buyer pool
A highly specialized layout, extreme size or unusual design may reduce the number of future buyers even when the property is objectively impressive. Liquidity matters most when the owner needs to sell on a schedule.
Separate lifestyle return from financial return
Family memories, convenience and privacy are real benefits, but they are not the same as investment performance. Keep the personal-use case and financial case in separate columns so neither is used to disguise the other.
Exit questions to ask before buying
- Who is the likely future buyer?
- How many comparable alternatives exist?
- How often do similar properties transact?
- What annual carrying cost persists during a long marketing period?
- Would the property be attractive without the feature I personally value most?
FAQ
Are trophy properties good investments?
They can perform well, but returns depend on basis, carrying costs, market depth and resale timing. “Rare” is not the same as “liquid.”
Should rental income be part of the thesis?
Only if rental use is legally and operationally feasible and the owner is genuinely willing to rent the property.
What matters most on exit?
Buyer depth, competing inventory, condition, uniqueness and the owner’s flexibility on timing and price.
Luxury note: Separate personal-use benefits from financial return assumptions and stress-test a slower resale scenario.
