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monkey123 if I had to take a guess, it's that gangsters are among the few demographics that are still super sexist. Sure you have supercringe fedora youtubers, and I would actually dig a manga about one of them in this situation, but off the internet they're the ones in the modern world who have the grossest opinions about what role women have. Them and high-level business CEO types, who often also get dunked on too by these mangas. (Youjo Senki, Circle Zero's Otherworldly Hero Business, etc.)
tl;dr -- the more sexist the guy, the more the payoff for putting them in a fish out of water situation. And the less the audience will feel guilty about uncomfortable things happening to them. Which is fairly problematic logic by itself, but I digress.
It's neat to see gender bender coming into its own enough as a genre to have recurring subgenres.