Should you decide to go with Canadian machines: first of all, good news! I work in a Customs brokerage office [I classify imports and send the information to Customs for clearance] and as far as I can tell, your servers should be able to come into the country duty-free.
Where it might get tricky: does your company have an actual physical location with employees in the States, or will the servers just be living in a building of their own where you'll work on them and then leave them? [Forgive me, I'm not sure how this works, exactly.] Also, would you be shipping them by themselves, or would someone from your company accompany them across the border?
Either way, computers fall under the realm of the FCC, and you'll most likely need to fill out form 740 [http://www.fcc.gov/Forms/Form740/740.pdf] and have it ready when making entry into the US.
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posted by alynnk at 11:36 AM on September 9