I think psychology is one of the issues. You go from being "particular" to ADHD, or chronically depressed, clinical anxious, ODD... And from those diagnostics most, I imagine, will typically end up on medications. It's the path of least resistance for the parent(s). Beyond that it can be used as an apparatus to excuse behaviors, or to broker certain exceptions. It can also become a narrative tool used to nucleate an identity, and that can be a hazard in some cases.
I don't think we do focus on individualism, either, and that's a problem. Proper individualism entails rigid personal accountability. Perhaps it's implied, and in effect what we've done is given a child a hammer without teaching them to swing it, no doubt many a sore thumb. In fact I really wonder if it's even probable that teachers can meaningfully interface with all but a few students.
I think workload has been increasing, and that's the anecdotal feedback I've gotten - harder work for younger kids. Less time for exploratory learning. Boys are perceived to have a significantly worse time than their female peers by their teachers. They also end up more disciplined. They're more likely to be "diagnosed" with ADHD than girls by a factor of two. Boys also experience higher dropout rates and juvenile detention. There's also an increasing rate of single mothers, and single parents just do not have it easy, women especially - and that puts more pressures onto the kids.
Support structures can be dogshit. Economy has moved. Families have been fractured and dispersed over long distances. And society doesn't really have the many support groups it once did. I can't speak statistically, but hearing about the dirt roads of the Denver Metro in the 70's and driving through it now, it's insanely packed. I grew up in rural areas, there were never any pretensions about danger or safety, and me and my friends wandered all over the town totally unsupervised as late as 2004. I don't know that such privileges are extended to these kids growing up in cities.
Expectations is another thing. Not only do the institutions make comparisons, they do it explicitly and loudly, but so do the kids. Yeah, the socioeconomic disparities I don't have any doubt play a role, but there's also kids watching these "perfect family" videos on youtube, watching super-human feats of every sort, egregious conspicuous consumption... And then they're just average, but the skew that such exposure introduces is, I can only imagine, pretty dangerous to some kids.
It's so multifaceted though. We've really got to look at the individuals holistically, track every step and kind of come to a real understanding of why they did it.