<get a high-level idea>: I'd suggest killing a Saturday evening or two by going through the materials for issuers at a relevant provincial securities website. I don't know about the Quebec securities commission; the BC securities commission has useful materials to read. There's a basic booklet now up on their website, but it's quite basic, so start there but drill down. Some years ago, Douglas Gray wrote a pretty good book about raising money in Canada. I don't know how up to date it is any more, but it's not a bad place to start for an overview, directed at a general, interested reader in the area, that goes into some of the technical law.
<securities lawyer in Quebec>: not off-hand. Try researching the people that Francois Rochon uses (Giverny Capital).
<how do securities regulations work>: It's a quite unpleasant area of law. Very Old Testament in its style, is the way I think about it -- "Do this (or don't do this), and you will die".
The basic requirement, though, is that the regulations apply to *both* sides of a trade -- so the jurisdiction where the issuer is located, and the jurisdiction where the investor is located. There are national policies that have been improved over the last 10 or 15 years, which help with ironing out some of the differences between provinces. But there are still provincial differences -- at times, trivial and unnecessary (Saskatchewan, I'm talking about you). Et bien sur, Quebec guards it's securities turf carefully. And there is *constant* change, so that it is difficult even for the specialists to keep up in the area. In general, the securities laws in BC, Alberta and to some extent Ontario are pretty good to work with -- so some smaller issuers will restrict their offerings to those three jurisdictions. I don't know how they compare to Quebec. Having to deal with the language difference is usually sufficiently offputting for most smaller issuers, so they give that province a pass.
For your specific questions, all I can say is get advice. There's more than one way to skin a cat. Because of the "both sides" rule, in the ideal world the issuer and the investors will all be in one jurisdiction. That keeps life simplest. Which in securities law is a good place to start from -- if it's possible (a big if, I realize).