Gaming and fooling regulators isn't a hard thing to do, smaller companies or small private planes might gamble and try to game them more often (after all, they got less money for compliance). Eventually it blows on their face and the regulators close the loophole but while the loophole/trick is going on, there is a higher CHANCE of a crash. It just doesn't show up in the crash statistics simply because crashes are rare. When it does show up (the crash occurs), its only 1 crash and regulators learn that they need to close that trick. Meanwhile all the risky flights from before are not computed. And the smaller companies/planes are trying to find a new trick again. It also appears that smaller companies have less experienced pilots so it doesn't help
The reason I'm bringing this regulator gaming up is because, its not only a matter of probability of small plane/company crash vs big plane/company crash. Everybody knows it is higher with the smaller ones, that is already taken into account the Sklansky theory by inputting the historical probability of a small plane crash. Its that if they do these sorts of regulator gaming and other tricks, the historical probability of a crash might be understated.
All the fights that didn't end up in crashes are not going into the crash database but while they happened, they had a higher chance of a crash. Eventually the crash happens and regulators put in extra precautions.
If they consistently game the regulators, eventually it will show up in the crash statistics. The problem is that if the dispersion is big enough (because they dont do it all the time, they don't do it consistently, etc), it might take a REALLY long-sample to have that appear in the data. So the historical chance of a small plane crash might consistently be understated. It might take (and I'm just guessing here) 100-200 years to have enough of a sample