And then get hit with a currency conversion fee? Probably would come out the same as if you'd sold back home.
Digital Nomads
If you do decide to do this, be safe. Offer to meet the buyer at police stations or busy shops.
Why would they be worth more?
Honestly, speaking from experience, trying to sell an Apple Watch, unless you get really lucky you won’t be getting much for it if it’s used…worth a shot but don’t get your hopes up.
In Brazil, absolutely. I have some experience with that. Use OLX to sell it. Lots of people will contact you if you sell at price that is low enough. It’d help if you have a trustworthy Brazilian friend that can use OLX pay for you, but you can also just accept cash.
US iPhone without physical sim card slot have value in countries that aren't migrated to esim (including the US smh, thanks Apple). MacBook keyboard layout is less of an issue for countries that use the same physical layout (Japanese keyboards add lots of keys, UK keyboards reshape the return key).
If you're going to rebuy after returning, I'd say it's not worth the risk. Selling high value electronics is risky even in the US, let alone Latin America. Scammers might pay in counterfeit currency, which is tough to spot if you're not familiar with the bills. Many payment apps allow buyers to chargeback the transaction later. The buyer could also just grab the merchandise, hopefully without harming you, and your only recourse is filing a low priority police report.
And don‘t forget to delete this posting when you claim the stolen Macbook and Iphone from your insurance!