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Good points all the way 'round. The article linked below, probably (unfortunately) behind a paywall, might help us think about answers to your "Tough questions".

https://www.wsj.com/tech/personal-tech/what-i-got-wrong-in-a-decade-of-predicting-the-future-of-tech-06420bba?mod=wsjhp_columnists_pos2

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