I'm not deliberately misinterpreting you, but I think I found where the disconnect is:

jwo is a different problem than the separate checkout kiosk you’re describing

jwo is the same problem as is in the image

I don't think this is the case. The berry box is somewhere between JWO and checkout kiosks, in that the density of items is small, and the background is clear, but there are multiple items at the same time. I'm seeing the items as discrete enough that it's more similar to checkout kiosks, but you're seeing it as more similar to JWO (now I understand why you keep bringing JWO up).

it was built to be accurate within the boundary of “no checkout step”

Was it? I mean in some sense yes, but I feel like it was primarily built for Amazon's image, to give the appearance of it working well. That's why they're secretly hiring people and claiming it's AI, after all. If they weren't doing it for their image they wouldn't even need to pretend that it was AI.

unless somebody moves or jostles them while taking some fruit

you’re essentially making the exact same naive assumptions about the operating environment that led to jwo’s failures

I suppose I am, but it appears that the person in the image is also making that same assumption (to the extent that the image is real-- it is satire after all). Having multiple items in the box would decrease the accuracy not only because of items touching, but also because the person could cover the box while jostling all the items' positions. You'd have to count every item before and after their interaction, and they could take 0, 1, or more items. It's definitely not as simple as I was thinking, you're right. Still easier than JWO imo but not as easy as the kiosks.

facial recognition is a thoroughly solved problem, at least in terms of the accuracy that we’re aiming for here

It's not clear to me whether it's easy to take fruit from the bowl without showing your face. It's certainly possible, but it depends on where the people are approaching from whether it's likely.