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I vote for "watch them in chronological order" myself.
The story changes from "The Journey in the Force of Luke" (if you only saw the original 3) to the much more powerful "Fall and Redemption of Anakin Skywalker".
You are expecting the child to watch them time and again - the clever bits like the evolution of the tech, the moments in the spoiler above and so on - they all bear multiple watching.
Each time he sees it he'll see something new in it.
Imagine this - you show him the origninal trilogy first then the new ones - he already knows that yoda can't die in 3. Ditto Anakin, Obi-Wan, Palpatine, Luke, Leia, Capt Antiles, C3-PO, R2-D2, Bail Organa, Jango Fett, and so on.
The tension in the Obi/Ani duel in Ep3 is MORE powerful if you don't realise that Vader is in the next films and that Obi makes it through.
There are issues either way round, but personally I think watch the story as it finally landed - not as it was made.
Also - Watch "Clone Wars" between Ep2 and Ep3. It's great, and it explains many of the tech evolutions that you see in the later eps.
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