When I first got my licence I decided that I didn't want to experience new difficult conditions for the first time on my own.
So every time there were new difficult conditions I shot off to the airfield and hired an aircraft (dual with instructor) to try flying in these conditions for the first time.
Within three months I had flown in heavy rain, snow, high gusty winds, and poor visibility, and several combinations of these.
This gave me good experience of what it was like up there, when viewed from down here. Not a perfect guide, but nevertheless a great help and benefit.
If the weather is iffy, I spend a good deal of time thinking all the options through, and make sure I have enough fuel and daylight (unless airways equiped) for all these options.
ps I have been flying today, (and almost every day this week).