I am thinking of purchasing a car in canada. It is quite a drive to go look at. I am considering (if i like it) bringing it back at the same time . The individual wants $20,000 for it. He wants cash but there is no way i am going to take that kind of money across the border. Does anyone know the best way to get an immediate payment like this to a individual. I also have a guy who would lend me a New York dealer plate. Would that be legal? Any other info on crossing the border would be greatly appreciated. Thanks

Check with US Customs before you make the trip. Also, "borrowing" a dealer plate is not legal, because you are not the dealer and the car is not being purchased for the dealer. Massachussetts should have some type of temporary transit tags, if necessary. I would not plan on driving it back. Rent a trailer and either take it with you, or make arraingments to rent one there and take it one-way (U-Haul). You'd be in quite a pickle if Customs decided to impound the vehicle at the border for a month or five.

Like Ted says, Check with customs before you do anything. They should be able to tell you what is required for any paperwork. Make sure you have it all! As far as payment goes, you can get an International money order made out to the seller. If you decide not to purchase and take money order back to your bank, it should be refundable but CONFIRM THAT WITH THEM FIRST.
And I agree, for that kind of distance, trailer it for the first trip home.
Just my $.02 (Canadian).
Dunc

i looked into this before. there is a us customs website as well as a candian one that will give you information. If i remeber correctly, you need to apply and have paperwork in order.

http://www.customs.gov/

I also found a word document (in the export section) that seems to have most of the info you'll need.
http://www.customs.gov/linkhandler/cgov/toolbox/publications/travel/importexportcar.ctt/importingacar.doc