return to canada for school/marriage after deportation

[saraya]

I've recently come to realize that I want to spend the rest of my life with my boyfriend, but there is a problem, he is an American and a deported one. In his younger (and alcoholic) days he made the not brilliant decision to live here in Canada illegally. In the early 90's he was deported. In 2003 he decided to try to enter Canada again legally at the border under the belief that the order expired in 10 years. He presented his legal ID, and for some reason nothing came up in the computers and they let him back in. However while here his ID was checked by authorities and he was deported again. Since then he has pulled his life together, clean and sober 4 years, worked full time until returning to school last year to study for his degree in economics and finance (still works p/t). He would like to be able to return to Canada to attend school for a semester or two within the next 5 years, if that is even possible, and within the next 2-5 years to marry me. Also we want to have a baby and in consideration of our ages, 37 both, we are considering doing it outside of living together for the first bit. He will be able to present references from a professor at his school and a pastor. I do not make enough money myself, as I am also student, nor will I after school (our Country does not pay educators well) but my parents who in retirement are pulling in about 50,000 a year will likely co-sponsor. Now my questions are, what are the chances that he will be let back in and issued a student Visa if he applies on that basis? If we have a child would he be able to return to Canada to visit? and what are the chances of his being allowed back here to 1) marry me? and 2) live with me (become a permanent resident)? Also what paper work would we have to file under each of those circumstances and cost? sigh...why I had to fall in love with an American I do not know, but boy did I ever fall hard and I really hope I don't have to become an American to be with him (but will if I must).