I get live weather with any start of a flight. My settings are:
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Automatic server
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Multiplayer = OFF
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Air Traffic = Live Traffic
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Weather & Time = LIVE
Then I click FLY and I do not change my weather when I am in the sim. I leave it at LIVE until I end the flight.
I then load a new flight with the same parameters and I always get Live weather. It’s been like that for me since the initial release.