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Agreed. The first scenario really suffers from conflating "boring" with "obsolete". If anything, most exciting technology has a much higher propensity to becoming obsolete than, and also long before, most boring technology does.

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Yes I think this is the key insight: if you have two technologies that will solve your problem, both reasonably popular and actively developed, the one that is ten years old is far more likely to still be actively developed in another ten years than one that is one year old.

You're using survivorship bias in your favour.

Well, only if both work about as well as each other. Good technologies are likely to outsurvive bad ones once the good ones get a minimum of popularity.

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