[cycleguy55]

The best document you can have is the original certificate of title showing it was complete and registered / approved for street use at least 15 years ago. If you don't have that you have work to do. Take a deep breath, be patient and persistent and you can get it done.

The date on the title generally is not sufficient unless the title date (not vehicle model year) clearly shows the title was issued at least 15 years ago. In my case the vehicle had been re-titled at least a couple of times so the date didn't work. So, on to Plan B...

Plan B was to search Michigan's records for the original date of first registration in order to document the age. Unfortunately, Michigan records are purged and not searchable after 10 years (or so I was told). On to Plan C...

Information on the Michigan Secretary of State's (MSoS) Web site indicates the VIN issue date is coded into the VIN, but not how to decipher the coding. I was able to get a letter issued by MSoS explaining how the date was represented in the VIN. The Canada Border Services Agency, acting for Transport Canada, accepted that as proof the car met the 15 year test.

Advice:
a) If you have a situation like the one described above use the Internet to search and read as much as you can about what Transport Canada is looking for, what you might be able to get from the relevant jurisdiction and what you can provide.
b) Be prepared to pick up the phone and spend a lot of time being put on hold, handed off from one person to another, and chasing down the various contact information you get.
c) Explain as completely and concisely as you can to those you talk to exactly what you're trying to accomplish and what you need. Be factual and don't exaggerate anything - you're trying to get them to understand your plight and get them to support your cause.
d) Stay calm, no matter how frustrated you get. Keep in mind the people you're talking to are operating in large bureaucracies and are probably just as, perhaps even more, frustrated than you are.
e) Take notes - especially who you're talking to and when (date & time), their contact information, what they tell you and the contact information they provide.
f) Patience, persistence and thoroughness will prevail.