If people who guess wrongly bemoan it loudly, while those who guess correctly enjoy it quietly, then all we will hear is regret even if most people get it right.

I think this goes doubly so online, where the loudest voices dominate.

This is why I have reservations about following online trends. It is only part of the picture of what is really going on. There is a silent (silent online) number of people who are just getting on with it quietly as you put it.

This captures a good part of the underlying problem with social media. It is often the disenfrancised and outspoken who dominate the discussion. Many of them don't work and support other activities such as families or hobbies, so they are able to spend that time complaining on the internet.

The article is making the argument that people guess structurally wrong. In the same way that it's perfectly possible under a waterfall design system that you manage to get all of your requirements mostly right from the start, it's also perfectly possible that a family is able to anticipate their needs for a house well into the future before having built/lived in it, but it's a structurally losing game.

An example of an alternative approach championed by a lot of people who want to build houses situated deeply into nature is that they'll live for the first 12 months out of a tent, shifting it to various places on their property. By doing this, they get a feel for how the sun behaves, where the wind moves, where animals like to roam etc. and make a much more informed decision of where to site the house. This is much more akin to the MVP/sprint model of building houses.

That someone enjoys their home is not enough to say they made a great choice just a good one. People grow attached to all sorts of things.

My personal experience is people are most likely to enjoy a home that’s easy for them to afford as it never feels like a burden.

"people are most likely to enjoy a home that’s easy for them to afford as it never feels like a burden" -- that is exactly my dream home.

Yeah, I’m living in my dream house but it cost me less than $500k. When I saw the first example was a $3.5 million home I stopped reading. It’s simple to spot people overbuying (read: guessing wrong). There are lots of people living in their dream homes they’re just not living in multi-million dollar homes.

I think it's fair to point out since homeownership can be a very poor decision if you aren't considering these things when you go all in.

People "guess wrong" about the perception vs. reality of their self all the time over plenty of things, and a lot of it results in them buying junk they rarely or never use. ("I'm totally going to learn how to shred on that ukulele.") Houses are just special given how royally screwed you are when you're trying to get some liquidity out of a several-million dollar asset you stupidly bought because you thought it matched your fantasy lifestyle and realized how wrong you were after it was too late. That said, I don't feel too sorry for these people, but I think it's definitely worth trying to teach others not to make the same mistake.