How Boomers Actually Got Screwed By Cheap Housing

The true cost of buying a house for a “pint of blueberries.”

Source: Pexels

Every once in a while I like to indulge in a bit of “nostalgia-gazing.” This is when you look backward and become wistfully lost in reminiscence. Maybe you look up old neighborhoods or homes you lived in, schools you attended, or places you used to frequent. You might even take a road trip out to those places.

During one such bout of backwards-gaping, I happened to look up a house my family rented way back in the halcyon days of 1991 located in West Chester, PA. West Chester is a quiet, middle class town with a few upscale neighborhoods and cul-de-sacs. It’s an idyllic place with a small town feel, located just 40 minutes or so west of Philadelphia. It’s still one of the places I consider “home,” even though I haven’t lived there in over 30 years. Such is the impact of certain places we live in as children.

Anyway, I decided to look up my old house–an abode where I once enjoyed a Jaws-themed 10th birthday party, where my friends all dressed as different sea creatures. I was the Great White shark, of course, as I was obsessed with the movie at the time. I found a link to the house through Zillow, and up came the house’s sale history as well as the current estimated value. My family only rented the house from 1989-1991 before moving out after the school year in June, after which it was bought in ’91 for a whopping $150,000.

That sure sounds cheap by today’s standards. Especially when the estimate for the current value of the house is $750,000. And that’s actually cheaper than many of the surrounding homes in the circle in which we lived. Some homes just across the yard on the next street over are well past the million dollar mark.

You won’t find much affordable in West Chester, PA today, unsurprisingly. Homes tend to start around $650,000 and go up rapidly. The town is a perfect example of what many Millennials and Gen-Zers (and I suppose some underperforming Gen-Xers, too) gripe about when it comes to the inflated price of homes.

“The Baby Boomers had it so easy! They had cheap housing! Why, back in the late 80s and early 90s, you could practically buy a house for a pint of blueberries! Now a house costs a first born and your eternal soul just for a down payment! I’m gonna rent until I die!”

We’ve all read the histrionic and hysterical pronouncements on social media. We’ve all seen the memes. It’s an outraged generational war cry: “The Boomers had it easy!”

But did they really? I don’t think supposed “cheap housing” tells the whole story. I think there’s a lot of ill-informed and misplaced criticism here when it comes to the affordable housing shortage, as well as some selective memory on the part of Millennials. It puzzles me sometimes seeing my generation so appallingly ignorant. After all, we were there, too. As kids, but we were there. Sure, I spent my days jumping on enemies in Super Mario Bros. and watching Saturday Morning Cartoons. But I was there. I remember the context of the supposed “easy times.”

My family was not rich. We were lower-middle class. Even the “low” cost of $150,000 for that house was too much for us. Hell, the house we wound up buying some years later in another area was like half that price. We struggled. I was the oldest of four kids. My three younger half-siblings were born 5, 7, and 9 years after me.

See, people forget that the Boomers were BREEDERS in addition to “cheap” real estate beneficiaries. Boomers did what people have been doing for eons–they purposefully set out to get married and have kids. My father had seven. My mother had four. My step-father had three (my three half-siblings). And they had those children starting relatively young. My dad was 18 for his first. My mother was 24. Most of my aunts and uncles had children, sometimes multiple, before the age of 30. It’s only recently that couples are having fewer and fewer kids. It used to be common to have three or more. My grandmother had eight, for instance.

And what do you have to do when you have a lot of kids? Well, if you’re responsible, you put them up in a HOUSE. A house becomes a priority by default. And not because a house is a “good investment” or an asset or whatever else the finance bros want to call it. But because it’s an absolute necessity.

And therein lies the first major counterargument against the “Boomers had it easy” mantra. Boomers were forced to buy houses because they had lots of kids. Kids need toys. They need their own rooms. They need yards. Kids need a lot of stuff, actually, and a house is the best way to contain all that stuff.

For most Boomers, their house was EVERYTHING. It was the black hole that sucked in all their available money. Most Boomers were not rich. They were middle-class. Most Boomers did not invest in the stock market. They did not buy gold. They did not buy silver. They did not buy bonds. Obviously Bitcoin and crypto did not exist back then.

No, most Boomers had a little savings account that earned maybe 5-6% interest, and their house. That’s it.

Today, it’s never been easier to invest in the stock market. Download the Robinhood app and in seconds you too can be FOMO-ing into the latest meme stock or crypto that some dude on the internet told you is “going to the moon, brah.” Financial awareness has never been higher than now. Go on Youtube and there are a million finance dudes who will happily educate you on everything from “diversification” to the “4% rule,” to the “FIRE movement,” as well as on more complex investment instruments like LEAPS, scalping, daytrading, and more. But who knew about any of that stuff back during the Boomer’s time? No one. Because even today the majority of people remain woefully ignorant on financial matters.

Today, investing in a variety of assets is seamless and nearly cost-free. Back in the ’80s and ’90s you had to visit a broker in person. You had to mail them a check. You had to pay PER stock transaction. And it wasn’t cheap, either. I remember as late as the mid-2000s paying $9.95 to Scottrade just to buy a few shares in Apple. Most exchanges today allow you to trade stocks at no cost.

Back then, almost nobody knew about index funds, mutual funds, ETFs, dollar-cost-averaging, “buy the dip,” or anything else. The typical Boomer investment portfolio was their savings account, a CD, a government savings bond or two, and perhaps a few physical stock certificates in IBM their parents handed down, some baseball cards, and maybe a family heirloom like dishes or something.

And their house, of course. Their house, that certainly took up the lion’s share of their assets.

And how did they do with those “investments?”

Well, on the surface, they seemed to do okay. The house that my family passed on in 1991 sold for $150,000 but today is worth a staggering $750,000. Wow. That’s a 500% return. That’s good, right?

No, that’s awful. So, so awful. Especially over 35 years. Even if the house was worth $1,000,000 it would still be a bad return given that time frame.

And that’s only looking at the base price of $150,000, too. Houses have ongoing costs. You’ve got maintenance, insurance, property taxes, and of course the interest on the mortgage. Over that 35 year period until today, my Boomer mom and step-dad would have likely put in around $300,000 minimum, which means they would have only just barely more than doubled their money.

Also, there’s a little thing called “opportunity cost” that makes this awful return even worse. Opportunity cost is what you miss out on by investing in one thing versus another. By investing $150,000 into a house you miss out on investing it in other things like stocks, gold, and silver. Remember, for Boomers, their house was it. It was harder to invest in even simple things like mutual funds. If Boomers had exposure to stocks it was largely through their jobs, which may or may not have had a 401(k). They might have had an IRA or a personal brokerage. Just like today, most people did not invest in the stock market. Or anything, really.

But let’s look at how some other popular asset classes did during that 35-year time period. From June, 1991 until now (March, 2026) the S&P 500 Index has gone up over 1600%. Gold went up around 1200%. Silver 1700%. And the Nasdaq Index went up an unbelievable 4700%.

That means the return on that $150,000 investment becomes:

S&P 500 – $2,400,000.
Gold – $1,800,000.
Silver – $2,550,000.
Nasdaq – $7,050,000.

In an equally weighted portfolio (25% in each asset class), the return comes out to around $3,450,000.

Suddenly, that supposedly large $750,000 becomes rather puny, doesn’t it? If you had invested your money into pretty much anything else except housing from back then until now you would have made vastly more money.

“But, but, but, Boomers were also able to invest in those things in addition to enjoying cheap housing.”

Absolutely. A small minority of them did, anyway. But if the statistics on stock ownership of today are any indication, many of them did not. Or if they did, they didn’t own much for it to really matter. According to Pew Research Center, 58% to 62% of U.S. households today own stocks. The top 10% of households own almost 90% of all stocks. The top1% own 50% of all stocks. While the bottom 50% of households own only 1% of stocks. That’s even with widespread frictionless trading apps like Robinhood and others, and the YouTube and social media algorithms giga-pumping financial knowledge bombs on you left and right. I’d guess that almost certainly stock ownership was probably a lot lower back then than now.

Yes, in the purest technical sense, Boomers got housing “cheap.” Not “pint of blueberries” cheap perhaps. But certainly way cheaper than today, nominally-speaking. And now they are enjoying much higher valuations on their homes. But at what cost? No matter how you slice it, a barely 2x return over 35 years is absolutely abysmal relative to almost anything else. Even a CD with a rate of 5% beats it.

My West Chester, PA childhood home represents a good average. Homes in Southern California, of course, and other places, have gone up a lot more. But you can’t just look at the prices and compare them to decades past. That doesn’t give the whole contextual picture.

The average Boomer struggled just like the average Millennial and Gen-Zer does today. They had limited passive income, or no passive income. And even if they were aware of investment opportunities, they had to sacrifice investing into them for the sake of their families’ needs (i.e. you). I remember my mom being very aware of Microsoft back in the ’90s, and mentioning how we should put some money into the stock. But we were so poor at the time that my half-siblings and I had to go door-to-door selling candy to help pay the bills. Do you have any idea what a mere $1,000 into Microsoft stock back in 1991 would be worth today? At least $250,000, not counting dividends reinvested.

In actuality, the Boomers got screwed on housing. They were forced to buy homes because they had larger families. At the time, interest rates were much higher, sometimes even into the double digits. So they were also forced into loans with ruinous rates. Having a house balloon into a million-dollar asset today is great, don’t get me wrong. But it’s cold comfort when looking at how much was sacrificed to get it. And how many decades it took. And then there’s the question of whether or not you can even sell it. Many homes today are stuck going unsold because there are fewer qualified buyers.

The Boomers are not faceless amorphous entities. They are our parents. Often, I think my generation and Gen-Zers apply too much bad-faith and cold-hearted criticism toward them when it comes to housing. When I think back to that house in West Chester, I just think of the house ten-year-old me got to enjoy a Jaws-themed birthday party. I think of the hole I dug in the backyard all summer for some reason. I think of the many friends I played with in that circle and on other streets. It doesn’t represent some great investment I was cheated out of. Even though I only got to live there for two years, I’m glad I got to live there for the time I did. If I could, I’d move there again. But I can’t afford it. And I’m almost a millionaire. Yes, that’s disheartening. I make a substantial income and have a solid net worth and even I can’t afford to live where I did as a child.

Look, the housing market is ridiculous today. No one’s denying it. But we have easy access to many other types of investments and opportunities with way better rates of return. Interest rates are much lower. We’re far more mobile now than people were back then. Many have the freedom to work from home. We have more options. Boomers didn’t really have a choice. They still had to contend with a lot of traditional social and cultural pressure on their shoulders. It was “get married, have kids, and buy a house.” Imperatives that many today, even ones with money, are ignoring or avoiding.

Should Rich Boomer Parents Help Their Struggling Millennial Kids?

A post on Reddit took the internet by storm with a polarizing question.

Source: Reddit

Are rich boomers greedy assholes selfishly clinging to their lifelong gains, or prudent individualists responsibly preserving their wealth to endure the unknown storms of old age and life in general? Were they simply the beneficiaries of better economic times, cheaper cost of living, and a jobtopia American culture, who bootstrapped their way to financial security through their own gumption, or did they cruelly pull the ladder up behind them and say, “Suck it, kiddos!”

Are Millennials lazy, entitled brats looking for freebies from mommy and daddy instead of doing the hard work necessary to build their own lives? Or ar they the victims of “late-stage capitalism” and all its ills: high cost of living, obscenely high real estate prices, and high college tuition costs? Are Millennials truly just fucked by the economy they inherited from their boomer parents? Are they working their asses off and still getting nowhere through no fault of their own?

And what about Gen-Xers? Do they even still exist? Or did they all just become Millennials when grunge rock died?

I’ve been thinking about the screenshotted post above all week since I saw it reposted on X. I don’t generally puruse Reddit anymore, so I get most of my viral soap opera content from Musk’s Madhouse.

The post prompted a lot of feedback. Some outraged. Some insightful. Some hilarious.

Here’s what Alex Becker had to say:

“The Wealth Dad” believes:

While others disagreed, and felt getting bags of money prematurely parachuted in from mom and dad would be a hinderance overall:

I don’t think anyone is entitled to anyone else’s money. Even their parents. Even if their parents are rich and it’s clear that when they die they are going to hand down millions, or tens of millions to their kids.

Are Millennials struggling these days? Yes. Many are. Are they having fewer children because of their struggling? Yes. Would a bailout from their parents help? Yes, it would. Money in your thirties, when many are building families or buying homes would serve much better than getting a bag of cash in your late 50s or 60s, after most of life has been lived. No doubt about that. And if rich boomers want to help, then by all means.

But let’s start with why so many Millennials are struggling today. For the most part, it’s largely due to student loans and real estate prices. And tons of bad debt. I myself had almost $35,000 of debt at age 30. Most of which was student loan related, but also credit cards and auto loans. I was truly fucked up. But unfortunately, I grew up in the lower-middle class, and while some extended members of my family, and ex-family, are quite well off, there was never anybody coming to lend me a hand.

I had to take the hard route. Packing up everything I owned in Philadelphia and moving to the frigid tundra of North Dakota. There, after some struggle, including brief homelessness and being reduced to one dollar to my name, I wound up securing a nice income in the oilfield. After two years, I had paid off all my debt, and built up a nice cushion of savings to finally go back to school and finish my bachelor’s degree. After checking off that box, I returned to work, and am now on the road to financial independence. I have zero debt, side income from investments, and basically have a “CoastFIRE” level networth. That means your retirement is secure via compound growth even if you don’t put another dime in of your own.

While I still have a ways to go until I’ve got that Holy Grail “Fuck you money” that everyone wants, I don’t think I’d have ever gotten off my ass and accomplished what I had if I thought mommy and daddy were going to help me out via inheritance or bailout. In fact, I’m way better off now than my parents are in retirement. I’m the rare Millennial who beat the odds and has done far better than his parents.

I rather like that. I like knowing I made it on my own without a handout. I won’t lie. Whenever I hear of Millennials who needed their parents to give them money for a house down payment, I look down on them. I think less of them. My mom and step-dad wouldn’t even fill out the FAFSA without giving me a hard time (a long story), despite apparently having “too much income” to qualify for it anyway. I paid for college entirely on my own. Hell, I moved out when I was 16. I did the best I could, fucked up along the way, but wound up course correcting big. On. My. Fucking. Own.

That’s not to say there have not been sacrifices. Real, killer sacrifies, on my part. For one, the oilfields of North Dakota is the place love goes to die. It’s virtually impossible to meet anyone up here. I had to sacrifice my prime dating years to pay off debt and secure my own financial future. Not an easy task, and not something every man is willing to do. It was very hard to try to have long distance relationships. It was demoralizing to make brief connections via dating apps, only to see them whither and die on the vine because of the distance, or because a girl I liked met someone else closer to her. Now in my 40s, I have to accept the fact that the optimal dating window has closed for me. Even if I am financially secure, that only goes so far once you’re past 35 as a man. I won’t accept garbage situations like single moms or women with baggage issues. I’ve never been sex-driven or needy or dependent on having a woman in my life. Again, a rare thing for a man. But then I’ve always been a loner and largely self-reliant. I was MGTOW before it was cool, baby.

I’d have loved to have met someone when I was younger and built a family with them. A financial bailout would have helped for sure. But what would have helped out a LOT MORE was the knowledge and training from my boomer parents about the perils and pitfalls of student loan debt, and some better financial education, overall. Both my mom and step-dad knew little about saving and investing, and so imparted no knowledge. I had to figure all that out on my own.

I think Boomers are highly overrated as “successful” or “lucky” because of the times they lived in. They had their own struggles, too. Be glad you didn’t have to worry about getting drafted into a war when you were a teenaged boy. My dad is a Vietnam vet. He joined the Army at 17 and later got sent over there in intel and recon. He was boots on the ground like the troops in Platoon. I’m very thankful I did not have go through something like that, and that all wars waged by our government since did not require a draft. I’m very appreciate and reverential of my father’s contributions. He is a war hero, and frankly, I’d be an unworthy asshole to act entitled to anything he earned from his Army pension or government pension due to his work as a probation officer for many decades. Same with my mom. She was in the Army also, and has worked as a teacher for many years, and gotten her own state pension and worked for her retirement. I love them both too much, and would much rather know they are secure in retirement than to think of them as piggy banks, to be used for my own needs. Again, maybe that makes me a rare kind.

Millennials have had opportunities that Boomers never did. The stock market has been far better, and more predictable, during our young adult lives than it ever was for Boomers. We’ve seen tech stocks like Apple 500X over the last twenty years. We’ve seen new asset classes like Bitcoin and crypto explode onto the scene. Broadband internet and smartphone apps have allowed us to navigate far more nimbly than landlines and payphones did for our parents. Real estate is way pricier in HCOL areas, sure. But the Midwest and South have offered cheap opportunities in areas that turned into boomtowns. The fracking boom saved my ass, and transformed West Texas and North Dakota into spectacular growth areas.

Even if you have rich parents, it’s never good to base your life on the idea that you’ll just get bailed out. At a certain point, you have to learn to rely on yourself. We’ve all met snobby trust fund pricks before. And we’ve all met helicopter parents who control every aspect of their adult children via money. Who the hell wants that?

Do some people have significant advantages from their parents because of money? Absolutely. But usually their success comes from their own intelligence and hard work. The money was just a tool. If I ever have kids, I’ll almost certainly leave something for them. But my real contribution will be to teach them how they can succeed on their own. Equipping them with the financial knowledge I never had. That’s a real inheritance.