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When filing a 1099-S for the sale of a vacation home, what do I enter as "original cost" if the home was financed and not paid off? (It was a timeshare)
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For original cost, you would use the purchase price of the timeshare/vacation home included any purchasing expenses even though the timeshare/vacation home was financed and not full paid off. Financing will have no effect on determining the capital gain or loss on the sale.
Since you received a 1099-S related to this sale, your will want to report this sale as the sale of a capital asset. However, if this was a personal use asset, the IRS will not allow you to recognize the capital loss on this sale.
To enter this as a capital asset sale in TurboTax, log into your tax return (for TurboTax Online sign-in, click Here) and type "investment income (gains and losses)" in the search bar then select "jump to investment income (gains and losses)". TurboTax will guide you in entering this information
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