I suspect, and I could be wrong here, that the reason YC associated so much value to those questions was that Power Law function which describes the ROI on their companies (so far) indicates that only 1 to 2 out of the 50 startups they fund (if that many) will be the ones worth investing in, the others can be written off.
So, PG and the rest of the crew probably looked at the limited supply of "Hits" that they had, and tried to identify, in their minds, what characteristics they associated with successful founders.
For whatever reason, the ability to overcome obstacles, sometimes "creatively", (aka "hacking the system") was one such characteristic.
They may also have had a few successful startups as well that worked "within the system", but I suspect those made up small percentage of their hits, and therefore would be much harder to predict.
From my limited exposure to very successful founders (Those who exit with an IPO or acquisition of > $1B), they are all mavericks willings to do almost anything to be successful. Many (most?) of them come very close to the line of what a reasonable person would consider generally acceptable , and they all have vast number of detractors, and quite often casualties and lawsuits on their path to success.
Think about the various legal issues associated with AirBNB - the AirBNB founders were funded, in no small measure, based on their unwillingness to let anything get in the way of success, and certainly weren't going to let some status quo/system which said what they were doing was wrong slow them down.
I'm sure it's possible to be a breakout hit, and create a $1B+ company while working within the system, but the large majority of times it's done (80%+), it's done by those who don't completely work within the system - ergo a demonstrated ability to work outside, increases your chance of falling into that 2-4% of very successful companies.