I'd actually say that while many of us might feel he sometimes overstates/exaggerates the difficulty, his statements are true more often than we'd think... just only for a very, very short period of time.
Delubrum Reginae's savage variant might've been harder than Baldesion Arsenal when it landed, but as soon as Zadnor landed and people started going in with Rays of Valor and such, major chunks of fights in the savage version of Delubrum started getting skipped. (I'd argue that Baldesion Arsenal retains some of its teeth because there's nothing after it in Eureka to allow for power creep, but it's also been out long enough that people have optimized the living heck out of it.)
I saw some true disaster scenarios in the first Endwalker MSQ trial in the first couple of weeks that Endwalker was out where the majority of people you got in there were on-level, not getting synced down; I saw multiple people just go "nope" and vanish, eating the 30 minute penalty when they got it in roulettes. Similarly, I saw some rough runs of Endsinger those first few weeks, when even the folks who went for higher-tier content were at most at i570, and the majority of folks were in i560 left-side and much lower on accessories, meaning they were closer to the minimum ilevel for the trial.
But it didn't take long before the majority of folks in that first story trial were at cap and being synced down, and raidwides that had seemed threatening to some folks no longer had much bite, because they were tuned with the expectation that it had to be a survivable fight if you went in with level 83 gear... which is worse than the Augmented Cryptlurker gear many folks exited ShB with.
Similarly, it wasn't too long before the folks you'd get in an Endsinger normal roulette included raiders in i600 BiS... and nowadays, even the folks who'd just hit 90 have often gone and bought i580 classical gear off the marketboard (since it's not really expensive at this point in the tier), and so are better-geared now than even the raiders were when Endsinger first landed.
Yeah, he's been way off the mark sometimes when stating the difficulty of something; P1S and Endsinger EX are both notable recent examples. But I think there's other times where he's been closer -- at least at first. So I feel like it's worth remembering that "difficulty" in this game is often a thing that can be readily circumvented by better gear (or equivalent, e.g. the Rays mechanic in Bozja)... and that tends to happen very quickly.
And that, I would argue, is a problem. Because even if the MSQ difficulty doesn't need to be ramped up on those who just want to play for story, the optional content that was meant to be harder also tends to lose its teeth very quickly in this game, leaving folks who do want content with more bite feeling at a loss unless they go run things Min iLevel No Echo.
(And almost no one runs anything MINE, unless it's for something like my FC's "Retro Raiders" crew who exist specifically to tackle older content that way.)