In summary, the Schelling point threshold for starting the SegWit theft is very high and only a sufficiently powerful mining cartel will launch it.
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the wealthy hate the masses, because the masses always want to steal via their non-meritorious concept of fairness. The masses take on too much debt, expect everything for free from the society/government, and then want to fleece the wealthy when their economic mismanagement ends up in economic collapse.
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The entire thesis of Bitcoin as a world reserve asset is that the nation-states are powerless to interfere with it because of jurisdictional arbitrage. So the wealthy have absolutely no fear of the governments nor the useful leftist idiots.
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Thus it is a necessary prerequisite that Bitcoin publicly demonstrate and boldly slap-down any fear of retribution from Marxists (i.e. the masses) before it will be fully respected as a form of Ideal Money.
The allegation of theft is a lack of technological understanding... if the miners of the Satoshi protocol accept these ANYONECANSPEND donations, they are not stealing.
I think it would be useful to summarize and highlight our areas of disagreement.
1) Schelling point threshold for a SegWit rollback.
I take the position that this will not be reached if Core slowly solidifies towards immutability over time which remains a probable outcome. You have stated that you view reaching such a Schelling point as a risk not a guaranteed outcome so we may agree here.
2) Powerlessness of nation-states due to jurisdictional arbitrage.
I think your analysis overestimates the power of bitcoin and underestimates the resiliency of human error. The fiat system may be slapped down as you predict but that process will likely give rise to something much worse. Jurisdictional arbitrage offers only partial and incomplete protection.
I don't believe Bitcoin is going to be boldly slapping down anyone. Instead it will succeed by failing to die. Any person who is wealthy and has no fear of governments is taking an unwise position.
I highlighted how I believe this will play out here:
https://bitcointalksearch.org/topic/m.35427611
3) The definition of theft.
Failure to secure ones money or failure to anticipate a theft vector does not mean the taking is not a theft. If I leave a pile of money unguarded on my front porch it may indeed be stolen and I may have no recourse but my failure to secure it does not mean the taking would not be theft.
Theft is and will be the primary concern of the wealthy which is why they would never support a transition to a system grounded in theft when superior solutions/transitions are possible. To borrow your language the Schelling point for such a transition would never be reached as there are other lower energy Schelling points that would be hit first and transition the system.