Re: TL;DR Nerdy Questions...
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Which, if any, books are "canon" that can talk about
how Chewy went into life debt with Han...?
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The "Han Solo Trilogy" might be what you're looking for. It's Han's story from a young boy until just before he meets Luke and Kenobi on Tatooine.
They were some of the first books written in the now massive Star Wars library. So, you can read them without knowing anything other than what's in the original movie trilogy.
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