Thanks for posting an interesting philosophical problem! Maybe there is an issue with the word "luck". It seems to be used in two ways. 1) in regards to initial conditions or things outside our control, and 2) in regards to good outcomes of decisions we make in the past. I totally agree with #1 that luck is involved, but #2 is a problem especially when I see people using it to diminish someone's ability to make a good judgement call, which was what I was getting at in my little thought experiment. For #2 I think it's not fair to call it it luck as there was clearly some choice involved. But honestly I'm not totally sure.