No, you don't need to add a line for each of the 30 items that were sold for a gain. You can enter the related totals for these items as the proceeds and the amount paid (cost).
To summarize:
The 1099-K entry for personal items reports the amount on the 1099-K, then adjusts that number to the actual remaining gain. The transaction you edit under Investments reports how much of the remaining proceeds is income from gains.
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