Not a particularly good strategy here for a couple reasons:
1) Risk on safety critical operations is not something people tend to want to roll the dice with.
2) The nature of the industry makes each trial pretty expensive. Over decades, the shuttle only had something like 135 launches and the managers still didn't have a good handle on the actual risk.
Sort of proving the point here, no? There is a reason SpaceX has gone to orbit more times than the Shuttle has. Soon they will have launched more Starship prototypes than the shuttle ever did. And they will be safer, because SpaceX understands why their rockets fail.
Obviously this strategy does not work with humans in the loop. It might have been impossible to do what SpaceX is doing now in the 80s given the advancements in computer control and simulation that have happened since then.
I don't think so, for the same reason you identified: it only works when the risk isn't safety critical (ie when humans are in the loop). In other words, it's acceptable when risks are low. It's the same reason NASA is more risk-tolerant with non-human-rated missions. But keep in mind CCP is also meant to transport humans. The risk we'd want to bolster against is the human biases that lead us to get complacent. There are some instances that make me wonder about that with SpaceX, but I'm giving them the benefit to the doubt that they've learned from those.