Bringing a Cdn. car back into Canada

I am currently living in the USA on a TN1 visa. I am thinking about buying a new car. My brother, who lives in Alberta, wants my used Jeep. I would like to give it to him, but I don't know what is involved.

1) The car needs to be imported back into Canada - it is a Canadian vehicle - who is responsible for that? Me - seller, him - receiver?
2) How do I transfer ownership out of state and out of country?
3) If it is a gift to a family member, are there taxes involved? In Canada or the USA?
4) What about insurance for the car to drive from NY to Alberta?

I can't be the only person who has ever done this. Any advice would be appreciated.

Are you planning to have it shipped? If so the shipper will help you with the details, but it amounts to this: if it was originally purchased in Canada, and you can demonstrate this to the Canadian border folks (e.g., with the original transfer of ownership or some other document showing it was bought in Canada), there's not duty. You do need to give the people on the US side of the point of entry you'll use 72hr notice of your intent to export (will be taken care of if it's a commercial importer). You also need to go chat with them before passing through to Canada to let them know you're on your way (they'll check the VIN and your NY title).
As to insurance for the drive, just keep the NY plates and the Alberta insurance people will trade you for AB plates once you go to insure it and transfer it to your brother (they should send the plates back to NY...at least that's how it happens in BC).

1) The car needs to be imported back into Canada - it is a Canadian vehicle - who is responsible for that? Me - seller, him - receiver?
2) How do I transfer ownership out of state and out of country?
3) If it is a gift to a family member, are there taxes involved? In Canada or the USA?
4) What about insurance for the car to drive from NY to Alberta?

Most of this is answered on www.riv.ca

When you say "Canadian vehicle" is it still registered in Alberta? If it is then the transfer is the same as if it took place in Alberta, basically.

Otherwise the transfer of ownership is probably simplest at the border, you are the seller, he is the importer. There may be Canadian taxes on it, probably GST. No duty because it's exempt under NAFTA. Sell it to him for the lowest practical value and give him a bill of sale perhaps, they do have bluebook values, if you're lucky they won't check when he explains the circumstances. Obviously it will be valued at over the $60 gift limit so GST applies after that. If there's no bill of sale then clearly they're going to go with the bluebook value.

Transferring the ownership at the border probably solves the insurance problem, because you're loaning him your vehicle until he gets to the border. What your insurance coverage says is then the relevant issue.