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Yes they will tax you at the border. Buy a used one down there with no tax. Say 2SS/Rs for like $33,000 - $35,000. then bring it across and pay GST/PST or HST what ever applies.
FYI
here in Canada a fully loaded 2SS/RS runs about $50,000 all in.
Edit:
You can change the speedometer to KM it's not a problem. The only issue with the car will be Daytime Running Lights (DRL) In the States there is the option of turning them off, here in Canada it's a no/no. DRL's must always be on there can be no on/off feature. You can bring your car to a dealership and they can run a computer flash to change that. Costs about $150.
My advice to you is do your home work. If you do it all right, just as Thrillz wrote, you can save up to $10,000.
Insurance:
That depends on a V6 vs. V8 and if it is your daily driver or not. Also depends on your past driving history of course. My Camaro is not my daily driver and I pay $900 a year to insure it.
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