Nobody leaves my property with my plates on any vehicle, no matter what the paperwork says. When he gets to the border check point, with Alaska plates on the TV and California plates on the TT, there will be questions. Even if everything is in order (bill of sale, insurance etc.), someone other than the crossing guard is probably going to have to OK that the Ts are crossed and Is are dotted.
EDIT: In Michigan, the plates belong to and stay with the owner. If I recall correctly, in California the plates belong to and stay on the vehicle. Don't know if a Canadian bourder guard would understand that, or how license plate transfers are handled in Canada.
