Success!

We survived Nestor with only a few hours of heavy rain. Lost our broadband for a bit, but that was all.

My third experiment was to applique the pumpkin with the Sharpie-drawn face and then embroider over the marker with black floss (I didn't do it as densely as I will with the full-size version of the pumpkin). I then quilted the pumpkin lines, back-stitched a stem, and blanket-stitched the outside edges. As you can see I think it worked best.

So for Oliver's bag I'm going to do a bigger version of the little test piece. For this I start with a piece of card stock (folded in half before I cut so both sides are symmetrical) as a template. I'll use this to cut out the solid orange fabric for the pumpkin shape, and then cut out the eyes and mouth to trace on top of the applique once it's sewn to the black center panel.