Before addressing your specific questions, we need to know whether the items you sold were personal property, or investment property. Personal property are items that you purchase without intending to sell them even though you may sell them at some point. Personal property is generally items that you use every day such as clothing, furniture, appliances, vehicles.
Investment property is generally property you intend to sell for a profit. While you may hold the property for months/years, your intent when you purchased it was to sell it for a profit. However, you don't have to sell such property for a profit in order for it to meet the definition of investment property. Investment property can be sold for a loss and reported as a loss on your tax return.
If the items you sold were personal property, then entering the information using the steps in your post is appropriate. However, for any personal items sold at a profit, that is, for more than what you paid, you will need to pay tax on that gain. Losses from the sale of personal items are not deductible. Keep records of what you sold so that if you are asked to provide documentation supporting your entries, you will have such information to provide. If you have not already done so, you might consider taking photographs of anything you sell as one form of documentation. There are probably other forms of documentation you can collect and keep which will also be useful if you are asked to support your entries.
You are correct in that if you need to report your sales, or even some of them, as the sale of investment property, you will need TurboTax Premium. You will have to report the items individually and enter the cost basis for each, the amount you received, and TurboTax will calculate your gain or loss. Thus, if all 200 items were investment property, then yes, you will have to enter each one as a separate item into TurboTax.
The sale of investment property is entered into TurboTax by selecting Wages & Income, left margin, then scroll down the screen to Investment and Savings. Select Stocks, Cryptocurrency, Mutual Funds, Bonds, Other, and thereafter begin to enter your information.
@stantonporsche
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