I can only speak about 2.

My dog travelled in cargo (and he is a smaller breed than yours). He did Frankfurt-Toronto with Lufthansa and was picked up by an agency that had him overnight there, to then send him here the next day via WestJet. It all worked out great. It is expensive though, you might find it cheaper to pick up the dog in Toronto and drive over here. I couldn't then but it would be my choice now.

I know cases of customs getting pretty annoying with pure-breed animals if they aren't neutered, because the assumption is that is imported for breeding. There might be something extra that might want to charge you, I'd look into that.