If a super wealthy person buys the wine, it is covered. That Gemara isn’t license to go crazy, but anything within reason is covered. My $7 bottle of wine (depending on my means) is covered, although I could use grape juice or Tokay.
Aseh Shabatcha chol is referring to someone receiving tzeddakah money, and I don’t think relevant to this discussion.
If the schools would install crystal chandeliers in the classrooms, it wouldn’t be covered, and if I send my kid in a chauffeured limousine it wouldn’t be covered, but that is not what’s happening.