I have a sort-of point system, as I might tone-down the scope of IMC I'd fly, depending upon recency of experience, and I'll sometimes call the flight off if there are pax and it is so windy or hot that it would be plain miserable.
But in general, if you never nudge outside the absolutely routine, you never improve skills, and stagnation breeds contempt, which in turn will kill you most surely.
Good topic, Ed.
Back in the day, when I started to fly ultralights, we didn't have much in the way of anything, so we didn't know what we were missing. Those who actually flew out of an airfield, a lot didn't because so many fields refused to allow ultralights to use their runways, we're amazed to discover that runways came more than 30 or 35 feet wide.
In those days, you learned to fly ultra light by listening to your instructor talk to you on a walkie talkie, while standing on the ground, beside the field you used for t & l. Many, if not most ultralights had only one seat, so there was no way an instructor went up with you.
Wind? Bring it on. Bumpy? Yep. It was very bumpy all winter and hot as hell all summer, with mandatory afternoon thunderstorms to fly around on the way home.
Then I got into the two seater and thought I was in the movie, Oklahoma, where everything was up to date in Kansas City and things had gone as far they could go. We organized fly outs all over the countryside and followed the rivers, lakes, or roads to find our way there and back.
We had excellent instructors who worked us over all the time to make sure we were flying safe and wouldn't bring a bad reputation to them.
I would love to see students start out with nothing but a six pack and do everything the old fashioned way, until they get it all down, before becoming technology dependent and losing all sense of adventure, self reliance and develop raw skills.