Should I move to Canada to be with him?

I have moved to the US 8 years from Estonia (Eastern Europe) and now I am thinking of moving to the great north (Canada) to be with my boyfriend. I will be leaving behind a stable job that I like (I will try to work out a deal with my employer to work remotely as an independent contractor – best case scenario), my condo (in this economy I am having to foreclose), business and some personal connections. My only hesitation about moving is my inability to work there legally. I will apply for a resident status, but the process will take up to a year and a half or longer.

My boyfriend is very supportive and told me that he will cover my expenses (car payment, car insurance, a few credit card bills (very minor)) until I can start working. He also is very supportive of me starting my own business which I wanted to do forever and never got the opportunity to (mostly time). I am a very independent person and have been on my own for a long time and having someone paying for me makes me uncomfortable as well. I just have financials doubts.

I really do care about him a lot and want to be together with him for a very long time… What should I do? Are my concerns legitimate?

Should I move to Canada to be with him?
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