Thai Bf Getting Into The Us And Canada

[meme]

Ok so the situation: I have dual citizenship in the US and Canada although I am Canadian and travel with a Canadian passport. I am currently living in Korea. I have a Thai boyfriend and would like to bring him home to the US for one week than on to Canada for 3 weeks.

He works in construction, makes a shitty wage. Is enrolled in an adult educational school because he does not have his high school degree and is trying to get it. He owns no land (aside from what his family owns but it is not in his name) and a motorbike that he is paying off is really the only thing registered in his name. His school and employer will both provide letters that they are giving him a months leave. Both my parents, one in the US and one in Canada are both well off are willing to write letters saying they would like to sponser him as a gift. They will also give financial proof of there funds. I do not live in either Canada or the US so I will also be going for a visit. He will have been to Korea and returned to Thailand within a month. He will have 1000-2000 Cdn in the bank.

So I guess I just want to know what are his chances? I figure if I get the Canadian visa first it would be a plus to prove that he will only be in the US for a week, on his way to Canada. Any advise is great.