He says "one of the best pieces of advice I've ever gotten is: Don't trade a gun for a snow machine". This is exactly what you're saying, and it's backed up by a lot of experience living without power and water!
https://www.youtube.com/watch?v=BH15Kua5P1Y&t=918s
He also says "everyone one of us has to decide when to jump ship on a technology"
He says canoes peaked in the 1960's, and you can buy a used one for like $125 that's the same as what you'd buy today for thousands. Same with hand saws. He maintains old saws and chainsaws and uses them:
https://www.youtube.com/watch?v=BH15Kua5P1Y&t=746s
when you look at any kind of manufactured goods a lot of things have reached their peak and are either poorer quality than they used to be or they're just the same quality as their peak
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I found this channel via a video about building an off grid cabin from scratch for a couple thousand dollars: https://www.youtube.com/watch?v=bOOXmfkXpkM
It's good -- a lot of it is built by hand with a hammer and nails. He even says load bearing screws are too expensive, and nails are better!
All of the advice reminds me of Taleb, because it's not necessarily trying to be "right", but rather distilling rules of thumb from practice.
The old one my parents had was aluminum with a metal gear. The modern version has been MBAed to death — the gear is plastic, and the lid is so thin that you could probably replicate it with 2 plys of aluminum foil. It costs more and is measurably worse in any dimension.
Grummans are great and they're still being made (though not by the original company).
However, for recreational/tripping/whitewater, Royalex-based canoes were better for a variety of reasons. Unfortunately the material is no longer being made because its intended use (Go Carts) didn't take off to the degree planned. The company continued to make it on a more or less breakeven basis but upon a change of ownership the new owner decided to scrap it. There have been one or two efforts to make something equivalent, but AFAIK they haven't panned out.
There are still plenty of well-made fiberglass/Kevlar boats being made but they're much more fragile.
Many preventable deaths happen every year as a result.
He says it cost me $100 to get the best that has ever been made, and it's backed up by a lot of experience living off grid
My personal take is that there’s a an apex for a particular generation of technology, and that is good forever. A 1930s Farmall tractor is an example of that... there are improved modern replacements, but the 1930 model still does the job near optimally. I would guess that a non trivial number of those tractors will be in use in 2130.
1980s/early 90s minicomputers are similar. Many of these devices are still in use today, and probably could be kept in use for decades to come.
Modern tech is a little harder because we’ve been in a rapid growth phase and the software services based world is more aligned with production than sustainment. I’d bet that trend will change in 20-30 years.