As long as none of the items were sold at a gain (if one or two things did sell at a profit, pull those out and enter them separately), you can enter them as one investment sale transaction/lot. Choose the option to list the sales individually (don't use the summary option or you will have to send documents to the IRS), but you can combine the personal items you sold at a loss. If you have any items that sold at a gain, enter the detailed information for those items as separate sales.
Anything you held for more than a year is long-term. Since these are all old items, choose an acquired date more than a year before the sale. Keep records of what you sold and your estimated costs for those items in the unlikely event that you are asked about the transactions. As long as you mark the sale as personal items and therefore do not deduct any investment losses, you should not have an issue or inquiry from the IRS. @johnmhtr
Personal items that you sell at a loss don't have to be reported at all, but since you received the 1099-K, this is just a way to report that tax form.
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