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having someone you trust who knows how to use the keys
That's already a tough combo to have :)
Afaik, having multiple backups for a single-key wallet is inferior to a multi-sig, and if we're going that road and we need to trust someone else anyway, why can't it be a Bitcoin company built to last?
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Everyone has their own life. I understand that in certain situations it is better to use custody companies. But the way I see it, it will always be the last solution.
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I understand your concerns, but with a little care you can overcome these "problems". Duplicating the backup in different places and having someone you trust who knows how to use the keys will solve your worries.