Cdn Citizen with US boyfriend wanting to immigrate....please help!!

[Canadian_Born]

I live in Canada & my boyfriend lives in the States.  He is wanting to immigrate as we are having a hard time being apart.  He's planning to "move" here in December (as a visitor for all intents and purposes), has given notice at his work in the US.  The plan is to get married in Canada and complete the paperwork for sponsorship of spouse.

I have so many questions, I'm not even sure where to start:

1.  How long does he have to return to the US between visits?
2.  If the paperwork is submitted for sponsorship, can he can an extension on his visitor visa based on "implied status"?
3.  What is the best way to coordinate all of this to get the best possible outcome?  i.e. he gets to stay here until the sponsorship / PR gets approved?

I can certainly support him in the interim and he also has an internet-based company out of the US...

Please offer some sound advice!!  I want to make sure that all goes well.....

[YorkFactory]

He may very well be turned around at the border if/when they find out he's quit his job.