I don't think you can accurately identify "good" weather for even a modest group of random people, because people want different things, for different reasons.

I don't think you can accurately identify "good" weather for even a modest group of random people, because people want different things, for different reasons. More likely would be identifying locations with similar weather/climate - or even partially similar; - X has weather very similar to Y; - A has weather similar to B, but gets colder in winter. Imagine trying to define a "goodness" of food. It's impossible. But identifying similar dishes is much easier and much more useful.