Ok, I have an answer and a divergence here
Ok, first how one of my old GMs did it, and it's a practice I've adopted is to occasionally roll 2d6. if it comes up doubles, something interesting happens. if it comes up double 6's, then it's something good. if it comes up two 1's, then it's something bad.
Example: Guy hits on hot girl at high class hotel bar. The charisma check determines how well she responds to him (and it turns out pretty good) I then come up with the possibilities, then roll 2d6 and look at the result. if it's doubles, she's a prostitute. if it's 6's, she's been prepaid to show someone the royal treatment, and she mistakenly thinks it's him (insert any plot device here you want, he could be mistaken for the extraction target, a dignitary's son, etc). if it's snake eyes, the prostitute's really a man.
this can lead to interresting situations such as
"so you lead her into your room, she's been holding your hand and giggling shyly at you the whole way. as soon as the door is closed, she runs her fingers through your hair and leans in to give you a deep kiss"
"Ok, I reach a hand around to grab her ass"
"as you hold her close, you feel something long and rigid pressing against you."
"Is it...?"
"Yep"
about a ten second pause, then he raises a fist and shouts
"I score anyway!!"
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Anyways, now for my diversion. there's a line from an anime I that I love,
Pilot "We're just gonna have to rely on my skills."
Navigator: "There's no skill here, it's a matter of luck!"
Pilot: "Luck is one of my skills.

"
I liked the idea of a character who was just naturally born lucky. kind of like a luck adept. Very few systems allow you to make such a character though, and I was wondering how people would suggest making one in shadowrun.
One idea I had of a downside to balance the upsides is that the karma costs for buying skills or anything are much higher. the reason is simple: if you're that lucky, you don't learn things, you don't even really pay attention, you just trust they'll work out for themselves.
Another possibility would be to modify existing edges/flaws for instance "sense of direction" you don't really know which way you're going, but if you guess randomly, you're right more often than not. Anything like college education that reduces defaulting penalties would be another example.
Just digging for thoughts.