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I too had noticed the prevalence of that position in Gary's work; I assumed that it was a customer favorite and that's why Gary uses it so much, since he does his homework as to what customers like. One plus could be that, visually, you can see the whole person on-screen, whereas in a fully bent-over position, sometimes it looks like the top half of a spankee is just sort of missing, from certain angles.
I can't relate to the stand-up position; it's not one I'd fancy being in, and it's never been requested in any of my play. Paddling usually takes place over furniture with torso against table or couch or high bed, OR with extended arms and hands on the seat of a chair or a low bed. In school, it was a grab-your-ankles thing, no furniture involved.
Personally, I'm more of an OTK fan. However, since OTK is so, so common in videos, perhaps the relative novelty of this stand-up trend is a bonus, that is, an industry niche of sorts.
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