Sorry for posting again, but I just realized that you can use the Gradient Tool, and it may be easier.
Put a new layer on top and set it to Soft Light, fill with 50% gray. Now, drag the Gradient Tool over it as desired. Adjust layer opacity as needed.
The problem you were having at first is applying the gradient to the mask on the image layer. Every place that the gradient was black you masked out the image so that it became transparent and the "checkerboard" showed through.
Gosh, that was easy! (And essentially what Damo77 was saying -- just took a while to sink in.)
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