Our 1099-S software supports this scenario. Please consider the following:
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If you are importing data from Excel or any other format make sure to check the box that says “Allow Duplicate Recipient IDs”, this way W2 Mate will accept multiple Transferors with the same Tax ID or (Social Security Number in this case).
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If you are manually entering the Transferors inside the software, a message will pop up warning you that the same SSN / Name already exists in the database and whether you want to proceed or not. In this case simply select that I do want to add multiple Transferors with the same Tax ID and proceed with entering the information.
Real Business Solutions Support Team, Makers of W2 Mate and Payroll Mate
708-479-8731