Good post.
I'll bring up two factors.
1) People ignore inflation in part because it's instinctive and in part because governments lie about the inflation rate. It's acknowledged that in the USA, the government deliberately drove down the inflation rate (using hedonics and substitution) in order to reduce wages and in particular to reduce social security premiums. The CPI in the USA also excludes food and energy, the housing component is spurious.
2) Government interventions are hard to predict. For example, housing has been a better long-term investment than it should otherwise be in part because many governments go out of their way to p'rop up housing prices as much as possible. Mortgage interest is tax deductible in the USA, and housing prices are not allowed to fall for long. A lot of municipalities restrict residential construction in order to maintain the prices of the existing properties, whereas in a free market supply would grow to meet demand. The placement of train stations, roads, and highways is often artificial and influenced by landowners wanting better property prices. And so on. In Australia, tons (TONS) of people own second homes that they rent out as investment properties, in part due to artificial tax structures. This has nothing to do with understanding market fundamentals or whatever, you need a political theory to predict how far the government is willing to go to p'rop up housing prices, or you need luck.
I read a biography on the Hemsleys a while back. They were a NY real estate family associated with 1980s greed excess. If I recall correctly, part of their wealth was derived from buying up properties near where they expected train and subway stations to be built, as those would soon rise in value as they became more convenient.
As for crypto, I sold half it as a loss but this was partly due to a (mis?)-reading of government intentions. I figured that the government was obsessed with breaking down crypto, and they have a lot of potential to do that. Governments in east Asia were making one anti-crypto announcement a week, a slow drip is much more effective at reducing investor confidence than a one-time, blanket ban. They can hire people to hack into crypto networks and exchanges in a clandestine manner, which will also undermine confidence. They can raise taxes on crypto. They can order banks to not allow transfers to crypto exchanges. They have a lot of means at their disposable to pop crypto if they want to, I took it to mean that they did and thus sold out a little. I may have been mistaken, we'll see.
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Enough posting for today !