The original meaning of this expression, it seems to me, is that one would rather be lucky precisely because being good is not a guarantee of success. For example, you sink an improbable, four-cushion billiards shot. Your opponent says, "Aw, that was just luck." You respond: "I'd rather be lucky." You'd be unlikely to employ this expression having just whiffed an easy corner-pocket shot.
As I said before, I think this is a stupid expression. We should all fire up the torches and hunt down Flyer's TA like the vilagers in Frankenstein. It seems to me that the study of Decision Science could be aided a hell of a lot more by emphasizing basic principles (like risk management, calculating opportunity costs, and the proper application of statistical regression analysis) rather than wandering through the weeds of what seems like busywork. I expect your next assignment will be:
The expression "There are lies, damned lies, and statistics" is widely heard. What does this mean? Stage an interpretive, allegorical modern dance wherein the characters of Mean, Median, and Mode struggle for dominance in the capricious world of statistical applications in social science, a world where research assistants pick statistical applications out of a magic hat and force an enslaved race of Numbers to perform unnatural acts. Try to incorporate the dramatic covention of a Greek chorus, but instead of using dialogue, have the chorus perform movement-based expressions of Cohen's Kappa.In my version, a poor Cosette-ish waif representing statistical significance is devoured by an evil monster called Tenure.