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In college
I used to drive-away cars for owners relocating from Northern Climates to Florida. Great way to get to spring break. Let me tell you the benefits of driving the Caddy owned by a brewery VP. The downside was no trunk space for luggage.
Seriously it can work out just fine or be a horror show. Depends on the people involved. Mine always worked fine and there were no insurance incidents. Not sure what the legalities should be in today's more litigious climate.
That was in the day you could hitchhike back. Now you have to figure plane fare back and one way tickets cost many loonies. It may be just as cheap to have it shipped.
One thing you may not have considered is the complexity of the cross border transit for either shipping or drive-away. In today's sad situation, the transit for a non-owner may be a bit of trouble. Can you pick the car up just on the US side of the border and import it yourself as the owner.
In any case, I'd get a bunch of pictures on the day the pick up is made sent to me before it drove off the lot just to establish the condition at pickup.
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