Upgrading version conventions

I'm interested in finding out what strategy others use on which version to use for production. For instance when should I upgrade 5.3.3 to 5.4.3 to 5.5.0. To me it feels safer to be on a version in which bug fixes have been applied. Is there a convention such as Stable is 5.3.3, Beta is 5.4.3, and Experimental is 5.5.0? Or should I always try to be on the latest release available.

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