Was there ever a generation that was largely "connected and happy," though?
You ask a very good question.
What Price, Privilege? / Has our overinvolved parenting style created a generation of kids with an impaired sense of self? If so, how can we work to get it back? discusses how today's children have an impaired sense of self. I agree with most of what is in the article, but not all of it. The sentence I agree most with is this: "Indulged, coddled, pressured and micromanaged on the outside, my young patients appeared to be inadvertently deprived of the opportunity to develop an inside." Another one is: "Authenticity is not aided when kids have to battle against parents who are implanting other, often unrealistic "selves" -- stellar student, outstanding athlete, perfect kid -- into their teenager's already crowded psychological landscape" as well as "Parents willingly pay thousands of dollars for tutors, coaches and preparatory courses in the hope that their child will outperform his friends and classmates and win an advantage in the classroom, the playing field or the admissions process."
In past generations, the sense I get is that young people were more connected to their peers in a genuine way rather than a superficial way. Many children today would like to have friends, but are isolated because they have little to no free time starting in about 6th grade. In years past, they spent time together after school in unstructured activities and were not inundated with 5-8 hours of homework, much of which is 'busy work' each evening starting in middle school. I don't recall any classmate or any of my siblings' classmates committing suicide while they were in K-12 or college. In cases where classmates had issues with their parents, sometimes they ran away or went to live with relatives, but I don't recall anyone choosing to end their lives at such a young age.
In the past, teachers that taught their subject matter retained their jobs, but teachers that just sat in the classroom that failed to teach were not re-hired year after year. Teachers graded homework and essays, corrected mistakes, and gave a wide range of grades rather than relying on parents to grade it or simply giving an A to all students.
In school, I can recall students participating in extracurricular activities not to build a resume for a college application, but because they genuinely wanted to participate. Mandated community service hours imposed by school districts to graduate high school were not required in order to get a high school diploma.
In the past, I do not recall teachers soliciting children and their parents for cash donations in order to give money to the teachers. Teachers were not allowed to tutor children for pay. I can't recall teachers working second jobs in after school tutoring centers getting paid directly by parents to tutor their children. The town I grew up in had no tutoring centers and no SAT prep tutoring centers.
Parents, especially in households where both parents worked, were simply too busy to be able to become over-involved in their children's lives. They were so busy it would be difficult to attempt to live vicariously through their children. There was no email back then and certainly no Facebook or Instagram or blogs where parents would overshare information about their children with seemingly Hallmark-inspired and sometimes photo-shopped perfection. Parents had their own set of friends and did not have to use their children as their companions. Starting in high school, in past generations, teenagers did not routinely "hang out" with their parents. Parents acted like parents, but did not dress like teenagers or attempt to look like teenagers. Kids were allowed to be kids, but in most cases not expected to be miniature adults.
