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this is like the sale of an auto used 100% personally. the tax laws say any loss on the sale of personal-use property is not deductible while any gain on sale is taxable. the same would apply to your golf club membership, the loss is from personal-use property and is not deductible.. perhaps that's why other than reporting proceeds the cost and gain/loss were left blank
Yes. The sale of a country club membership is treated as a sale of stock or an asset. You should receive a form 1099B on the sale of the membership and it should be reported on Schedule D, Your costs would be what you paid for the membership and the sale price or proceeds would be the amount the membership sold for.
For Box 1b (Date of Acquisition) use the date that you first become a member of the country club and Box2 would be determined based on how long you have held your membership. It is short-term if you held your membership for less than one year and long-term if your membership was held for more the one year.
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