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The term "retired theme" is one we borrowed directly from StudioPress. Themes come and go, and over time some theme developers elect to stop updating a particular theme. A theme will not stop working because updates are no longer being made, but as more time passes, the risk of something breaking increases. Since we might have clients using themes that became retired or have prospective clients who want us to host sites based on a retired theme, we keep them around. We know their days are numbered. We just don't know how big the number will be before it's time to remove the theme completely. Perhaps "retired theme" is a polite way of communicating that it's time to break your bond with your old theme and start putting a fresh coat of paint on your site.