Adam Back: Two Bitcoin interviews (back-to-back)
Crypto Voices
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Is It Possible to Soft-Fork a New Proof of Work?
Software doesn't have checkpoints in it, but has hints as to which is the correct valid chain. When there's a major software upgrade, they update the hint to a blocker that multiples developers verify and sort of start. And so, by the time the old hash function actually degrades to the point of failure for the hash cache use case, which may or might not happen, then you're already protected by several more years,. So, I think that on a long term like that, it's reasonably safe.
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