You could manually enter the enter the Sales Proceeds as Schedule F income, and Depletion as a Miscellaneous Expense.
Click this link for more info on Reporting Timber Sales
Yes, an operating loss year after year can raise a flag at the IRS.
This link has details on Schedule F.
TurboTax does not support Schedule T, used for reporting a 631 Election.
@Loblolly
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