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U.S. citizen immigrating to Canada to live with canadian citizen boyfriend

My situation is such that my boyfriend and I have been "communicating" for roughly 8 months. We have been together during his interviewing process in the states. He is in his last year of medical school in Israel, and I have followed him to finish out the year. He match for residencey at the University of Toronto and has asked me to be with him. I understand the particulars when dealing with border control and the proper terms to use. The problem is that I need to make money and I'm not sure how to go about it.

1} Do I need a job before getting thee work visa?

2} Because my boyfriend is going to be a doctor in Canada and is obligated by law to be in Canada for the next 5 years, is there something that can be done to help obtain residencey in Canada using this info?

3} I am in Israel until late May and I would ideally like to get started on any paperwork and processing now if at all possible.

HELP!!!
 
With the information that you provided, it would seem that the only way to get into Canada and work is via one of the formal work related schemes. As it stands at the moment, you would not qualify for sponsorship as a member of the Family Class. You should therefore be looking to enter under your own immigration route, as though your boyfriend was not a factor.
 
For your boyfriend to sponsor you, you have two options:

1) Apply as common-law, which you can do after you have been living together for 12 months continuously

2) Get married and apply as spousal

Otherwise, as zardoz said, you'll have to sort out your own immigration route.