Regarding the opposite (shipping from the USA to CR) which has been mentioned here a couple of times. Pretty easy way around that. A good friend of mine now living in CR permanently had approached a couple of guys about bringing stuff down. The guys all got a little scared about being a shuttle service. But customs really doesn't care about that.
As a Platinum frequent flier on United I get 3 free checked bags. I almost always bring down just a carry-on or maybe one checked bag. Now I almost always have one checked bag full of my bro's stuff that he orders on Ebay or Amazon. I take the stuff out of the boxes to save space and bring all the receipts. I declare EVERYTHING unless it's like a small stuffed animal or something.
As long as you're not bringing down 50 iphones or something ridiculous like that, but just some stuff that one or two guys might need, customs really doesn't care. I just say they're gifts for a friend (the absolute truth, from a certain point of view). Often, the customs guys don't really do anything except wave me through. Occasionally, I pay a duty, but it's still way cheaper than buying in CR or having it shipped.
My buddy almost always comps me a first-class upgrade (when it looks like I won't get an auto upgrade), a couple of nights in Jaco, and a taxi. Pretty much a win-win situation.
This could also work CR-USA, but I would expect the USA customs guys to be a bit more tight-sphinctered about it. Still, you get $800 duty-free, and even if it's all the same item, you could always say it seemed like the perfect gift for anyone, and so you bought a bunch of them to dole out to all your friends and family.
The job of customs in most countries is to prevent illegal imports and tax-free funding of major sales outlets. They are not looking to bust the guy that's bringing in one or two laptops or a few bottles of Victoria's Secret perfume. However, they may still (just depends on your luck, their mood, etc.) charge you a duty tax to enter the country with it. Worst thing is not to declare if you have 3 or 4 laptops or a whole suitcase full of that VS lip gloss that the girls love.
Of course, if you're doing this as a business, you need a reliable stream of people coming and going.
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