In the past, I've brought my devices to the Apple Store to be traded-in. I think that's the way to do it as an Apple rep looks it over and quotes you a trade-in price. There is randomness in hassle factor though. Sometimes it's as easy as accepting a quote then you get a gift card. At one time I had an Apple rep (who just also happened to be unfriendly) wanting my license to process a trade-in.
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Hmmm, that's an interesting strategy. This time I would buy new because of the scissors keyboard vs. butterfly, but in the future . . .
Also, maybe a two-year old or a 1-year old, but we couldn't AppleCare on those though. I thought of refurbished, but feel a complicated electronic item like a laptop once brought to be fixed can never be fully fixed. But then again maybe some of the refurbished are simply laptops from consumer who had buyers remorse??