South Park 2016's "We were completely wrong in 2004, please learn from our mistakes" stuff was basically the problem in a nutshell. This is a problem borne of the current 18-25yos growing up under a Dem pres as voters and not understanding the problem with the alternative.
And it's a different set of 18-25 year olds every few elections. This is a cyclical issue (much as you describe it as systemic), much like how we see 3rd parties read their heads as a problem in those same elections.
I was 12 years old in 2000 and even then I knew there was a huge difference in who won.
People just, as I said last night, lack intelligence and/or empathy. It's possible for people to gain both, but most people don't want to bother.
I do agree with that. Hell, I see it not only among family and such but even in my students, who by dint of their racial and immigrant backgrounds are pretty damned good about some issues but still harbor and espouse stereotypically wrong views of minimum wage, gun control, etc. A lot of them share a surprising amount of overlap with white, conservative voters in some disturbing ways.
And yea, we've mentioned this before but I was 14 during the 00 election and Bush's win infuriated me. But I was an oddly politically attuned kid thanks to a couple of great teachers and my family (who I spent all of my teen years arguing politics with).