Insurance
Andy, I have found that US insurance companies can/will not insure cars in Canada.
Perhaps you need to operate under the same system that covers cranes, vacuum excavtor trucks, truck mounted tree spades, etc. here in Ontario. They do not have license plates & must be insured as off road machines. If you could come up with a legitimate farm use for the half track your farm policy should cover it on the road. I drive my John Deere to town once in a while & it is covered by Farmer's Mutual. Your White would certainly pull a wagon load of carrots through a wet field where many tractors would not.
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