So this is a guy throwing every random statistic he can find without checking any of them and still somehow arriving at Rich Dad, Poor Dad. No, he's not wrong: capital accumulates, labor does not (that one predates Marx & Engels). And no, he's not wrong: it's been a lot harder to be in the middle for a while now and it's getting harder. From a literary standpoint I would have gone with "these are the costs I'm facing" rather than "these are some costs I've googled" because then he wouldn't have gone ballistic bemoaning the $110k/yr cost of a Stanford MBA (average salary $220k/yr 3 years out of school) or harping on the $8k cost of having a baby in hospital when it's actually over $30k (over $100k if you need a c-section). But then he gets to

Now, that seemed strange to me at first because I remember reading a bunch from 2008 to 2013 about Quantitative Easing and how the Fed was “going to print a ton of money.”

And it seems like it’s true, they did “print a ton of money”:

But unlike the prophecies of talking cartoon bears, all this money didn’t drive inflation through the roof and crash the stock market. It doesn’t seem to have really gone…anywhere. It just hit the banks’ deposit reserves and sat there (right-hand graph above). Two trillion dollars, perhaps slowly winding its way down now, in excess of what banks are required by regulations to hold onto.

From all appearances, on every metric, any way you can slice the macroeconomic data, this whole process seems to have been managed…if not perfectly, at least as well as any person could have reasonably accomplished.

Champagne all round for the people who work there, and I really do mean that. No sarcasm, no cynicism.

SO HERE'S THE THING.

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Ben Bernanke did his doctoral thesis on the Great Depression. The Great Depression was his thing. It was his hobby, it was his subject, it was his area of expertise. And when Lehman went tits up, Ben Bernanke saw the Great Depression and, because this was all the studying he'd ever done, concluded that what caused it was a liquidity trap. We've gone roundyround about liquidity traps before - very simply put, that means nobody has any money to lend, so nobody has any money to borrow, so nobody has any money. Solution: print money (but not so much that you end up with Weimar deutschemarks burning in the stove or Zimbabwean dollars for sale on eBay).

There's that "2 trillion" your boy talks about. It wasn't 2, by the way, it was 12. You can google that shit. "US total quantitative easing". And we had Cash for Clunkers and we had TARP and we had refrigerator rebates and all that shit but we also had extremely low interest rates (something like half the money in the world is currently under negative interest rates, something not seen in the history of banking) which means borrowing money gets cheap. Probably not cheap for you. I mean yeah my in-laws' mortgage was 12-fucking-percent and mine is 2.5 but that's like $100k or some shit. Chump change. But I mean -

Do you know what a "bond" is? It's a loan. There are a million complex ways to slice it but fundamentally it's "I would gladly pay you Tuesday for a hamburger today." And there's $12 trillion of extra liquidity floating around. And the bond market is 40 trillion dollars.

That thing Bernanke and posse did? They basically made it so that if you were a member of the investment class, you got a 25% bonus on your money so you'd keep spending it. Remember - this is after the investment class blew up the world with subprime and all the rest. American households lost 16 trillion dollars - an average of $70k per house. Investors gained 12 trillion dollars and now HOLY SHIT EVERYTHING IS EXPENSIVE FOR THE MIDDLE CLASS. Let's see that quote again:

Champagne all round for the people who work there, and I really do mean that. No sarcasm, no cynicism.

There's an adage in investing that, like most adages, is unattributed: bear markets return money to its rightful owner. That's exactly the opposite of what happened in the 2008 crash. It had been getting worse for a while but Main Street took it in the ass for 2008 and they still haven't got theirs.

So to your question:

doesn’t economics tell us that some competitor would, seeing all those juicy college tuition or housing profits, come in and outperform/overdeliver or otherwise lower prices for consumers?

No. Economics tells you that competitors maximize profits. If the market rate in San Francisco is $8000 for a 1br, and I can build student apartments that cost me $1000 for a 1br, I'm going to make $6999 in profit on every bedroom I have, mutherfucker. More than that, if I charge less than that I'll be throwing money away because if everyone cares only about price they'll do anything to save a buck so if I'll end up with just as many tenants at $7999 than I would have at $1001.

As far as college tuition, there's a Frontline for that.

Why then are all these consumer segments getting more expensive than everything else, for nigh several decades now?

That's a broad question. List the sectors you care about and I'll do my best. Warning: I'll probably try to tie it all to the repeal of Glass-Steagall.