I make high middle class money and I don't know anyone in my peer group who has "A 2500 sqft house, two (or three) cars, regular vacations to Europe or the warm south, maybe a summer house, boats, motorcycles AND other toys".
You are describing the upper echelon of lawyers and execs.
Yeah, our household income is ~30-40% higher than the median for our state (WA) and with two modest cars, a 1300 SqFt home(in an "up and coming" neighborhood, lol), student loans, a new baby, and very, very few electronic devices (our phones are our most expensive computing device - and we only have a small 26" LCD TV), we barely squeeze by, or so it feels. We don't vacation at all, at least in terms of going to Europe - we might road trip to Vancouver, BC for a weekend once a year.
Also, no other Toys - I have a weight set (power rack, olympic weights, heavyweight bench, etc) that ran me 1300 brand new, other than the car and the house that is our most expensive purchase... ever. I could have sworn once we reached a six figure income we'd be "well off." I guess that is a dream.
I'm going to go out on a limb with an assumption: the fact that you hang out here probably says a lot about you and your socio-economic status and general intelligence, which relates to your financial sense.
But there were/are a generation of blue-collar, "middle class" people out there living the life I describe. I know some of them. They aren't lawyers and execs, they're public servants, unionized factory workers and such, most of whom make less money than me. Their boomer parents were middle-class wealthy, and their expectations are higher. Only the economy no longer supports it. So they fulfilled these expectations via copious amounts of debt. Then everything broke.
You are describing the upper echelon of lawyers and execs.