The price tag is the smallest number in the deal

Each of these purchases comes with a second, permanent price list that runs whether you use the thing or not. A vacation home means taxes, insurance, association fees and maintenance every year, in years you visit twice and years you never go. A boat means dockage, storage, insurance and maintenance. A timeshare means annual dues that creep up every year, attached to an asset that is notoriously hard to sell at anything like what you paid.

None of these are bad purchases in themselves. For a household with a fully funded retirement, they may be exactly what the money was saved for. The problem is timing and honesty about the total cost. Bought on the emotional high of the first year of retirement, before the new budget has settled, they quietly convert flexible savings into fixed obligations. A decade of dues, fees and upkeep can consume the equivalent of years of planned spending, and unlike a portfolio, these assets cannot be partially sold when you need cash.

My suggestion is simple. Rent before you buy. Spend a season with the rented house or boat, add up what ownership would truly cost per year, and see whether the dream survives the arithmetic. Many do. The ones that do not were never going to make you happy as an owner anyway.