I don't know. You buy players because you believe they will improve the team. I appreciate some turn out even better than we imagined, but when you look at the signings of Prior, Sodje, Gray, Goater & Bailey as well, all of these had massive contributions in our uprisings, even Clarke once he started playing regularly in his natural position. Signing Barrett and getting 10/11 goals as well as a solid die hard defender is another example. Yes he had some bad signings too, but the number of players he signed that performed over and above expectations can't be purely down to luck. Eastwood was exceptional, granted, but he still needed managing, to nurture the talent, to continue to improve the player - remember this is a player that fell out of love with the game previously. He even dropped him at one point because his attitude started to wane, then Eastwood came back with a vengeance, starting with the winning goal at Blackpool from the bench.
I refuse to believe that the three cups runs and two promotions were down to him getting lucky off the back of two signings. The tactics were naive at times, and his substitutions left a lot to be desired. But he pulled the team out of a relegation fight, and built a team that gave us some of our best years as a fan using his tactics. He bought the key players, he picked the team, and he trained them. It's seems massively disrespectful to him, and the rest of the team; Goater, Sodje, Prior et al, to attribute it to getting lucky with the performances of just Flavs & Freddy.
I think if you can attribute any of Tilly's success' to luck, it would be the lack of injuries we suffered during our glory years, allowing us to maintain a settled team and subsequently momentum. But even then you could argue that it was down to good training and player care from the back room team.
As unlikely as it seems, if Sturrock pulls us out of this lull we're in, dragged us up two divisions, took us to two cup finals and a League Cup Quarter Final via an epic giant killing, I'd hope we'd be a little more respectful than to say he just got lucky.