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Yes they will ask even it 2000 and do not try to hide any thing or u will be doomed. If u have till 10000 that included the stuff u carry as well so u will be checked in and out and u need proof of document for that so safe to do is bring proof and just bring 9000 or so because they will check...

Its not that much they are the same averadge around the world like 40 to 50 usd per limit transfer like if the normally its set to 2 to 3000 dollar and its every where in the world even from here in canada more then that they ask to may details and question where money came from how u earned it...

There is a legal way to do it and the easiest way just send it through wire transfer from the bank yes who ever is transfering if he is a tax filer there will be no problem 1 year back i transferred 50000 cad to my canadian account from pakistan it was easy but i was a tax filer there as i do...