Sure, I was mostly just dicking around with your phrasing with the non-exclusive-or answer to "X or Y". Just didn't expect it to be noticed much.
I'm not much for flowery language, so question about a caterpillar mourning? Nope, caterpillars do not know about cocoons or their meaning.
As a question about perspective, sure. But I'll double down and throw it back to you - the perspective of the unknowing caterpillar is just as good a metaphor as the knowing caterpillar. The dream of the butterfly as an allegory of unknown transitions into or out of unimaginable, inaccessible states is just as easily described by the caterpillar who doesn't know what a cocoon is. We don't know what the events, objects, environmental queues are that will be transformative in our lives, or what the signs are that someone has transitioned in a similar way. It's only with hindsight that we see the key elements, such as getting in our cocoon, that lead to our butterfly transformation. At the time, we had no idea what a cocoon was, even as we were building it.