Have you read the last few of these essays posted here? Every single one of them I've read can be summarized as such: "I wish to focus on a certain characteristic. I will hint or explicitly state that negative qualities of said characteristic are found predominately in fields I do not care to work in and often have a negative stereotype about, and also hint or explicitly state that positive qualities are found predominately in fields I do care to. It so happens these positive qualities tend to be qualities I am ascribing to myself in this essay, or have ascribed to myself in the past."
Here is a choice selection:
"Do the earnest always win? Not always. It probably doesn't matter much in politics, or in crime, or in certain types of business that are similar to crime, like gambling, personal injury law, patent trolling, and so on. Nor does it matter in academic fields at the more bogus end of the spectrum. And though I don't know enough to say for sure, it may not matter in some kinds of humor: it may be possible to be completely cynical and still be very funny."
There's very little to be charitable about when reading that. It shows a profound lack of consideration for the fields and topics PG is dismissing out of hand, to the point where one seriously wonders whether he's actually given any more thought to it than whatever reaction from his own youth he's channeling in the moment.
Then there are the unsupported assertions that litter these essays, and they're all more or less alike in character: "Nerds in high school become Kings in adulthood". It's actually not only trite, but overbroad. In some ways it's true, but in many others it's not, but PG tends to generalize the former in his essays.
It's easy to insist on being charitable, but it's a bit harder when there's just so little to work with.