I know it doesn't always work out, but it definitely helps to keep current, rather than performing a massive update every X years. Most of the time the changes are minimal, but they add up over several major revisions.
Of course, every now and then something like eslint will completely break every project in existence by changing the configuration format, then you have to wait for all of the plugins to be updated (if ever), then hope all your linting rules are still valid... yeah I'm still bitter about that one.
I just moved an eslint config from a project started a little over a year ago to a fresh project and migrating the config took up way more time than I expected. The old config had options that didn’t make sense in the new config, or that weren’t covered in the migration docs, etc. I think it all works now but who knows if some odd rule got missed and that’s just that from now on
Of course, every now and then something like eslint will completely break every project in existence by changing the configuration format, then you have to wait for all of the plugins to be updated (if ever), then hope all your linting rules are still valid... yeah I'm still bitter about that one.