Myself and my wife both had fathers that were in the trades. So even in normal times there wasn’t much extra money. But during times when there was no work things got tight. We both had the mentality coming out of college. We paid our college loans off as quick as possible. We worked hard and climbed the corporate ladder a bit. We were conservative with funds always worrying about the worst case scenario. Overall it did us well.
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I guess we are fortunate that while we grew up with fairly modest means, we saw the rewards of saving even as kids. Most of my sibs are savers, like we are but also like and acquire some nice things plus go on vacations that invariably involve flying (hey we live in an island).
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Related are research findings that growing up poor teaches someone to prioritize immediate benefits over future ones, because there is no indication of likelihood of getting to the future where one can enjoy the future benefits.
On the other hand, some who grow up “poor, but not dirt poor” (i.e. with some degree of stability in life, rather than worrying about the next meal or whether they will have housing next week) may acquire frugal habits out of necessity and continue them even if they later have higher income.
There may also be effects on those who grew up in high income families for whom high spending habits are “normal”. But such spending habits sustainable on parent income of $300k may not be on a new college graduate’s pay levels.
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In some families we’ve known, the “budget” method is to curtail expenses to fit income. When circumstances improve, they have to learn to set some aside for savings.
It could just be that the parents were practical about the value of a college education. Maybe they could have afforded an $80k/year private college but realized that the same degree could be had at the $30k/year in-state college 
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OP, I totally get this. When we were new parents, renting a pretty nice apartment, we would pass big houses with giant playsets and I sometimes would cry – what do they do, I ask, that we are not doing?
My DH would remind me that loans exist, doctors and lawyers make more money than librarians and teachers, and that we will “drive our own car” . We have never been rich, but are proud that our kids didnt have student loans and we managed to make that happen.
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In this particular case, it wasn’t how the conversations went. It was about affordability.
I marvel at anyone who has never wondered about other folks who seem to have so much (there I go again, being in awe of others). I’m not jealous, just curious.
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Oh, I would think most if not all of us are Curious - but it’s a slippery slope from that to Envy or Jealousy. I would also put the curiosity in the other direction though. If someone makes X and feels like they need to stretch every dollar look around at people that you think have less and wonder what they’re doing (or not doing!) to make it work.
My occupation is in corporate budget/finance. With an admittedly small sample size I find that most people that end up jealous of other peoples financial situation have never sat down to do a personal budget and track where they spend their own money.
I guess it depends on what you mean by wonder. I am by nature and vocational training curious so, yeah, I always wonder lots of things but it’s nothing I dwell on. For instance, my neighbors got married at 15 and 17. He never graduated HS. But they’ve built this awesome life for themselves with some expensive trappings. I guess I wonder whether they can really afford them or are they in lots of debt, but I’m mostly just proud of them as I know they had difficult upbringings.
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I’m curious from time to time, usually if they are very young. I live in a neighborhood that has small stone cottages as well as enormous mansions. When I see a baby swing hanging from a tree branch in front of an enormous mansion or see a young couple with a baby come out of their house to go for a walk, my curiosity is piqued about how someone so young can afford that. The thoughts are very short lived, however.
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We used to live in an upscale commuter suburb - lots of professionals and corporate executives and such. One benefit was that I was able to get much of son’s toddler/preschool toys at yard sales, and lots of his clothes at the village resale shop (also clothes for me). They were able/willing to spend retail for a year or two of usage; I didn’t have to.
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Our current (and former, too) neighborhood is a hodge podge of homes of various ages and sizes, from 2 br 1 bath fifties ramblers to ginormous Ballard boxes and anything in between. When older homes go on sale, the neighbors always get curious. Usually it means a new box or two will pop up soon. Most of the time, it is a builder using a spec plan. Occasionally, someone goes big. Like building a grandiose spaceship-like home that was definitely a special architectural design. You bet neighborhood residents check public records for that stuff!
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I once commented to a coworker how during struggles I try to remember there are others who have things some much worse. His reply - “Yea, but it seems always easier to notice those who have it better than you”.
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But then many people seem to actively avoid living where there may be people who are poorer (or whom they otherwise see as “lower”) than themselves. The presence of an apparent homeless person can trigger an avalanche of calls to the local police, even if the homeless person is not doing anything illegal.
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Really that is it. Most of the time I see things and just try to see if it makes sense. Like down the street is a couple with kids, but they both always continued to work their professional jobs and had Grandma Rose watch the kids. They in turn have a fleet of BMWs in the driveway. Smaller ones, but still like four of them.
I just sometimes do a double take when something doesn’t track.
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BMW’s depreciate like CRAZY - you don’t say specifically but good chance that fleet of BMW’s are all a few years old and they need a fleet of them because 2 of the 4 are consistently broken. 
Or maybe the in-laws own a dealership and those are “borrowed”. Or maybe they prioritize driving a nice car over some other things.
Natural to be curious of situations that don’t track and/or when you see people make financial decisions that are to an extreme of one that you might make. I just don’t give it much thought beyond that.
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The BMW comment reminded me of when my kids were young. There was a family with one boy. Both parents had really nice cars, while I had a Subaru or maybe Honda. When I dropped my son off at their home, I was a little surprised to see they lived in a very small townhome. Nothing wrong with that, just wasn’t what I expected given the cars.
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I have a cousin whose in-laws gave her a nice car for Christmas one year when she had just finished grad school. Pretty sure she too caught some notice for that given how incongruous it was with the rest of her life! I always thought it was so lovely that they wanted their DIL, who really had faced a lot along the way, to have some luxury in her life.
I am naturally curious about people, so this kind of thing intrigues me! Not in a judge-y way but as “how did these end up as your choices?”
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