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I believe that "pretty" in the context of weather is very non-standard use of that word; when I hear people praising the weather, they will say "good" or "beautiful", but not "pretty"; "pretty" is in much more common usage as applied to little girls, or pictures, or gift wrap. "Pretty" is more frilly and frivolous, "beautiful" more serious, higher value. People would be very hesitant to call a boy "pretty" (probably also not "beautiful" but rather "handsome") because it would diminish his masculinity. I also think, in most of your examples, "beautiful" would be preferable to "pretty"; the words actually have slightly different meanings.