Are you in EU? Because there's no import duty on laptops in EU (some sort of WTO agreement from 1996 IIRC), so there's only VAT to be added. If you aren't, I must admit your situation is even worse... and I completely agree, there're many people who buy laptops abroad and no one asks them about it. I think it should be legal, as long as you aren't bringing more than one and it's unpacked (meaning used, meaning you can't sell it as new). Besides laws that aren't possible to execute are demoralizing

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Trust me, if the dollar went up they would've adjusted prices before you knew it. And there're many companies who adjust prices annually no matter which way currencies go (i.e. IKEA). Apple resellers only lower prices when they absolutely have to - new models are coming and they realize they still haven't sold their fist shipment...
And besides it goes more like $1999 * 1.19 * 1.09 = 2592. It'd be too good to multiply by 1.09%