That's not what I said. First, the IRS could care less about individual transactions. However, whether you are or are not in a business and you sell and item of property for profit, that profit has to be reported. Expenses in connection with the sale may be deductible. E.g., when I sell my beautiful but rapidly aging Mercedes 280 SL I will add to my initial declared value capital expenditures to reduce my profit. However, if those expenditures exceed the profit, I cannot claim them against my other income since I am not in the business of selling cars.