Driving to CR - anyone done so? (San José)

UPDATE - have decided against driving. And have found I can take my dog in cabin. So as soon as I have all my ducks in a row I'll be on my way to a new life in CR.

I am in southwestern Ontario Canada and am planning on moving to CR before the next cold Canadian winter! I don't have much I want to bring with me other than my dog. He is too big to fly in the cabin and I don't want to have to put him in baggage for Protected content (the only direct flights do not take pets). So I am considering driving. Has anyone done this? Any advice is welcome.