This is a completely non-political post/position. I think there has been a significant shift in "lifestyle" expectation for the upper middle class.
I would consider my upbringing to be upper middle class. I grew up in a very basic house in a very basic neighborhood. My parents drove basic cars - ex. a midrange minivan and a "nicer" sedan that my dad's job mostly paid for. We didn't go on lavish vacations, just went to Wild Dunes for a week or two every summer (local beach). I went on one trip that required an airplane my entire childhood - to Disney. We didn't have fancy things, lavish decor or anything out of the ordinary. "Summer camp" consisted of riding around town on my bike or a junior membership to the local crappy golf course that cost about $100/mo and I could go play every day.
Fast forward to today. It seems that people believe the lifestyle that accompanies upper middle class needs to include a pair of Yukons in the driveway (or other expensive vehicles), homes that are farrrrr more expensive and nicer than what I grew up in, instagram-worthy vacations, expensive camps, etc. And the biggest issue of all - keeping up with the Jones' on social media.
So I have no doubt that it "seems" harder to make it financially today. But I also think the expectations have shifted significantly, not just the cost of the basics.
I had a similar upbringing though it was probably more basic than yours. My father played football in college as an OT, joined the Air Force, had a nice career and then had a drunken driving car crash that led to a traumatic brain injury that affected his motor skills and ability to process information, so he joined the USPS and was a mailman for the rest of his life, while my mother stopped working to take care of the kids.
Because of this, our vacations revolved around wherever his yearly postal conventions were held - Houston, Hattiesburg Mississippi(twice) and a couple of trips to the beach. We never had fancy cars, clothes or niceties that the upper middle class had and I never took a plane flight until I became an independent adult. However, I wouldn't call us poor because he made great investment decisions and had a million dollars when he died. But it did teach me a lesson about frugality, saving and investments.
I enjoy my life and travel much more extensively than they did, including a trip to Spain in a few weeks, I have a fairly nice four bedroom house and bought a new car last year that I paid off, but I wouldn't call my lifestyle lavish. Though I do feel the pinch more than I did in the past and have dialed back my spending in other areas. So even though I'm fine, I understand the vibe people are feeling that things aren't that great at the moment.