Risk/reward depends on the usecase of course. For a startup I’d be on the .1 version of the newest major version (never .0) if there are new features I want. For enterprise, probably the oldest LTS I can get away with.
If you have a large code base and organisation then keep doing those upgrades so it won’t be a problem when it really matters. If it’s painful, or touches too many areas of the code you’ll be forced to refactor things so that ceases to be a problem, and you might even manage to contain things so well that you can swap implementations relatively easily when needed.