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Alright so I've gotten some more research done. I found that wikipedia actually has a lot of the sentencing information for Canada which is making the search a lot easier for that. In their wikibooks section they have the Canadian Law Code

Going through the checklist it seems like we are on the right track.

A couple of questions in regards to documents:
For #15 on the application listing the convictions/offences it asks for the statue numbers. Would those be the codes from the US or Canada? If they're from Canada can you give me an example of how it would look written out? I know NYS would be: PL 140.20, etc.
Also, if this list ins't the Canadian equivalent then where do I list the equivalent offenses?

For the certificate of dispositions, do they need to be the originals?

He has a few letters of references but, most are dated for 2015. Should we update them?

The personal statement for the circumstances for each arrest: since he has 6 spanning from 2006 to 2010 does he still need to provide information for the oldest ones?
The other personal statements for being rehabilitated and purpose of trip to Canada should be separate, correct?

Sorry if these are dumb questions and thanks for the help!