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My guess is that it started simple. Early caterpillars probably didn't metamorph into something so drastically different. Even earlier ones probably barely had something that resembles metamorphosis.

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They likely didn't metamorph at all - it would've started as "since you're just going to moving as fast as you can so you can find a mate, burning through fat stores faster is good...also thinking about it, you're not going to miss that mouth you're not using anymore either?"

There would've been some sort of weight/reproductive efficiency trade off going on (and it would've been heavily environment dependent).

I might be wrong, but why should the caterpillar be the first to evolve? We don't have issues with the idea of an embryo developing into a winged animal, e.g. an egg into a bird. Then it's not that hard to imagine that eggs, in certain favourable conditions, could evolve the ability to absorb nutrients from the environment before hatching. And that behaviour could be optimised until the egg might become able to move and feed by itself before completing its growth into a bird. And you have some sort of bird-caterpillar.

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