If you're OK getting a 16 year old TM, the import process is really easy. Before you go down, go to an insurance place to get a "binder". This allows you to have it on the streets in Canada. It's like temporary insurance. When you go down to get it (if you do) make sure you get a proper bill of sale, find proof of its age, and make sure it is licenced to tow in all the states you would be going through.
Then be prepared to pay all the taxes!
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