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If you want more for your AW just put an add in Craigslist or one of those for sale apps. Apple is just buying it for the components so if you trade it to them think of it as a $100 trade in discount and not selling your old watch to them.

In terms of upgrading your Apple Watch from the S4 to S5, and your idea of selling it on craigslist, you will not accrue more. Craigslist is the most well-known site for people to haggle hard. If you want to make the most, you probably would have a wider audience like sites like eBay with A demographic of somebody who’s willing to pay your price based off the condition.

Local buyers are looking for the ‘best price possible’, Craigslist is the pinnacle of never generating what you want for the Apple Watch, especially seeing how quickly they depreciate. Swappa and eBay will maximize the profit. [Pending condition, accessories included, ect.]
 
If you want more for your AW just put an add in Craigslist or one of those for sale apps. Apple is just buying it for the components so if you trade it to them think of it as a $100 trade in discount and not selling your old watch to them.

This.

You will absolutely get more money on CL than you would trade it into Apple.

Some people here might have different experiences - and yes there are hagglers - Just reply and say no thanks. They might come back with a reasonable offer. If not, just hold tight.

I just looked at my local CL and the cheapest used S4 I can find is $470 ($335 USD) right now. All S4 and S5 are basically $500 and above here. And Vancouver Canada isn't a small city. Honestly though, if I was the buyer - for these prices I'd rather buy it new than be looking for used on CL.

Put it for sale a little above what you'd like to get for it - let the haggler come, then counteroffer in the middle of the difference and you're done. Much easier than shipping on Ebay etc...

 
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I would wait for AW6 if I had a 4.
AW5 LTE is my first one, but battery life is not awesome. If it going to be a long day, I turn AOD off.
 
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