Entropy is a metric targeted in LLM training which is likely why LLMs are overfitting less and less as they improve and why they subjectively seem to obey Occam's razor.
There's lesson for software engineering in general behind that kind of simplicity. https://benoitessiambre.com/entropy.html
But your smarter data scientists will try to get the best information density on test data to approximate generalization. MDL, as championed here, or AIC/BIC if working with more established and acceptable methods.
For complicated hypotheses, where complicated is defined appropriately, it takes many many examples to realize that it was a wrong hypothesis all along. There lies the rub.
For a particular instance of a learning problem we can't tell much, however using a Occams razor over many instances, one would be correct more often than not. Provided, of course, the PAC assumptions are true or they are not very far from being true.
How far is not very far ? That gets very hairy to quantify.
More typical definitions of simplicity, e.g. using the bit length of some kind of natural encoding, aren't guaranteed to offer any special advantages in terms of likelihood. So if you have prior knowledge that a particular hypothesis is more likely than another, but the less likely one is simpler in an intuitive sense, you shouldn't let that override you, but still prefer the more likely option. (And you don't need to take the circuitous route of coming up with a new encoding where the more likely hypothesis has a shorter bit length, either.)
If you say, and I think you are indeed saying so, that PAC is ridiculously pessimistic, I would be in violently agreement with you. That's one reason why for practical training data sizes and practical (infinite version space) hypothesis classes PAC gives bound such as -- probability of error is less than 41K. This isn't exactly incorrect but not very useful or informative.
A far more useful formulation is PAC-Bayesian where you get error bounds less than 1 guaranteed and usually less than 0.5 on reasonable sized training data sets.