This is counterintuitive, but in the framing of the article, I think that "y'all doin okay?" would actually be part of Guess culture, not Ask culture. It's just a very up-front manifestation of dealing with Guess culture, I think..? It's not Ask culture because the person who needs something is not doing the asking.

This is abstract, but stay with me here

I'm also Southern, and I think that the inclination towards that kind of belligerent helpfulness comes from trying to figure out what your guests want, and making sure they don't have to ask you for anything.

in my experience the response is "we're all good out here, but thank you!" -- which is classic Guess culture