Yeah. For me I've usually defined it as "it's tough enough that you feel a point to gathering your friends to do it together, but not SO tough that you can no longer afford to simply take your besties because you need to recruit your group like it is a job or you don't stand a chance."
But this is in turn also a function of one's own skill level. Personally, as a veteran gamer, I'm pretty handy with games, and even put in a fairly good showing in MMO raiding in former days - but I'm older now, have less time and energy, and my life schedule is not good for static play anymore. So the high end raiding stuff becomes increasingly a source of stress rather than fun (especially now that being "handy with games" is no longer really enough - we're at the point where the kind of tricks that used to normally be reserved for competitive speedrunning are practically expected, and given how many Savage+ raiders swear by Those Tools, arguably, we're getting close to pushing human limits: in most game communities the equivalent to week one Savage prog would even probably have to be labeled as TAS and be counted separately from "proper" play).
But due to having much of my past moxie still, casual content is usually too pedestrian (unless it's got some specifically tricksy bit in it, then I start to stress because, hey, it's casual content! You're supposed to be finding this easy! Are you sure you aren't just BAD, Miyako?).
This is a problem on both ends. Rewards did not used to be such a need. Remember older JRPGs where the reward was literally just bragging rights (like "Proof of Omega" from FF8)? Now everything needs a functional reward for some reason, you even see it in the FF mainline series (e.g., FF12's Wyrmhero Blade, which you get way too late to actually make any practical use of, but apparently, Yiazmat and Omega needed REWARDS!).
Yep. An outsized, almost arrogant at times seeming valuation of personal time at the forefront, combined with a loss of social camaraderie. Even pick up groups used to be much more fun and lively. Now nearly everyone treats teammates as hired help who exist so THEY can get THEIR personal goal, and any delay is "not respecting my time" to the point that onboarding new players, for instance, is someone else's problem (ie. Duty Complete PF) to the point that people frustrate out once the supply of available "someone elses" thins out (now a positive feedback loop to the point that people almost have to plan their work PTO around content drops, which leads to even more salt when, say, SE has to delay a release and it's too late for people to redo their vacay).
LOL I know it was a throwaway line, but surprisingly relevant: over the years I've noticed that most of the people who had contrary opinions to the community hivemind have pretty much just gone with the "well but whatcha gonna do?" angle and forced themselves to conform with it for the sake of unity (or just quit XIV altogether). Only diehard firebrands like me are left after that, and at that point one's point hardly matters, the contrariness alone is enough to be picked off as a "troll" in most modern communities, especially the heavily centralized ones we see so often lately.
Flip side: This sort of learned helplessness customer mindset trend (where, in many cases, it seems that any customer who isn't entirely satisfied and still has the courage to complain about it is branded a "Karen" now) isn't that good, either.