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As a lefty, I have found it's very easy to address this problem by turning the paper 45 degrees to the right (i.e. 12 o'clock becomes 3 o'clock). Then your hand rests beneath the writing line, and you can use more of a pulling effort than a pushing effort, and your hand is relaxed. No additional hardware required! The only time it's a problem, is when signing contracts and the person offering holds onto the paper at the top, square with the edge of the table.
A suggestion, before you start sewing across the hole, sew around it with running stitches, making a ring slightly larger than the hole. Pull gently to restore the shape of the sock in the area of the hole, which will also reduce the area you have to fill in with the darning stitches.
Great idea! I'd use it for canned goods...would bungie cord work instead of dowels? Easier to get stuff in/out and a bit more flexible as to width?