There's a lot of these extensions.json files in sites/default/files/civicrm/upload/cache, some with really old dates, but nothing seems to be newer than June 2022. Can I delete them?

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Yes if you're on 5.52 or later. (Or even if you're not it's ok - it will just make a new one when it needs.)

Storage was changed to SQL storage in 5.52. See https://github.com/civicrm/civicrm-core/pull/23768. So there won't be any new such files created and you don't need them. You can also delete timestamp.txt.

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