I've experienced this on random occassions too. I just sold two weapons in Highkeep Hold and didn't receive my 16 plat. A week ago, my gf ranted about not receiving any money at all for the patchwork she vendored.
The patchwork was gotten through the crushbone orc belts.
The weapons were simply vendor-bought ones, and since I didn't need them anymore, vendored once more.
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