If I was to make a speculation...
I would say that a long time ago, skateboarding involved mostly placing your front foot at the head and using your rear foot to propel. Since most ppl are righties...their stronger foot is the right so it goes in the rear.
After decades of snowboarding and the diminishing of skateboarding as a result, this "goofey/regular" balance has evened out gradually as the original advantage of regular stance isn't really relevant anymore.
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