I went down to Boston area last October and brought home my 560SL. There is a LOT to learn here, but I'll cut right to the chase.....Firstly, if the car is less than 15 years old, you'll need to go through some hoops to have changes made to bring it into compliance with the b*****t regulations under the RIV program (Registrar of Imported Vehicles), mostly bumper brackets, daytime running lights, speedometer KPH stickers, stuff like that.
Secondly, if the car is a Mercedes, and is less than 15 years old, only Mercedes can make the changes (everyone else, almost, can have Canadian Tire do the work)(no, I'm not kidding)....Well, you think, that's reasonable....but wait, there's a set rate to make these modifications from Mercedes: about $7000.00!!!!!
When we brought our '86 560SL to Calais ME for the 3 day wait (for US Customs to check vehicle for theft)(again, lots to learn here), there was a beautiful '96 SL sitting on the lot. I asked the lot owner about it, and he said it had been there for 3 years and he had just recently bought it from the owner, who was from Nova Scotia. The guy had purchased it in Florida, didn't do his homework, and had to unload it...for about what I had paid for mine.
Here's a couple of links to get your research started. You won't find this outrageous conversion fee from Mercedes though. I learned this from the guy at the storage place, and have since had it mentioned on several other forums
http://www.importcartocanada.info/
http://www.riv.ca/english/html/how_to_import.html

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1986 560SL
2002 Toyota Camry
1993 Lexus

Its funny you mention impact bumper regulations I work at trade school in alberta(specificlly in the Automotives and Heavy equipment area).We often get cars donated from many different manufactures to be used for what have you. Last year we had one of the schools facultys do a project on 5kph front and rear impact crash tests to find out how various models faired. It was suprising to see the results. I beleive 1 model made it within the $500.00 range (assuming you could find someone to paint and prep a bumper for $500.00). The worse case was a border line right off with structural trunk pan and quater panel damage. In seeing these results first hand it seems as though this is an out dated or maybe a third world country(cheap labour) law.
Getting back to import rules it sounds as though the 15 year rule is the way to go? maybe I will wait tell a 96 300e is 15yrs old. I wonder how a 15yr old car becomes magiclly safe and compliant to canada standards...
thanks gary

That may or may not include the cost for Mercedes Canada's "Letter of Admissibility". MB Canada can confirm price. There is also a cost to do the safety estimate; according to MB Canada, "Estimates for safety certification work are only available through an authorized Mercedes-Benz dealer in Canada (charges may apply)."

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ARVY

1999 E430
1999 C230 Kompressor
1992 300E (write-off)
1984 190D 2.2 (sold)

well tonight I took a serial number off a car for sale on ebay and sent it off to mercedes to see what all they will tell me. by the sound of some of the feed back Iam starting to think it would be better to buy 15 years or older

Let us know how it goes. Good luck!

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ARVY

1999 E430
1999 C230 Kompressor
1992 300E (write-off)
1984 190D 2.2 (sold)