Residence permit for Germany

Hi everyone. i'm italian living in germany. my boyfriend is canadian and planning on coming to stay in germany with me.what possibilities does he have to get the recidence permit.will it work if we get married as i am italian? and my other question. my boyfriend is working as a teaching for an online school teaching southkorean kids. will the german work office recognize this as a legal job?i'm asking because it's an online job so it's not a job which will make him work for a german employer. can anyone help me? there are so many questions and every office seems to give me a different answer.

I can't actually help much with any of those questions. I believe if he has a job lined up in germany, then being able to stay would be easier, but as it's an online job, and I'm assuming he's not paying taxes (to the german government) I can't imagine that they would view it as employment in the sense of giving him residency. Perhaps if he were to sent himself up as selfemployed . but that's a pain in the rear as well. And I couldn't say if it's possible.
Does he have English* parents/grandparents? That made it easier for me to stay here in Germany. With Eng. parents, grandfather (grandmother if he's born after 1984) he can get a British passport, which helps. He still will have to show the Amt für Öffentlicheordnung that he's employed though (or at least I had to when I came over 9 yrs ago). It seems a very tricky position you guys are in.
Of course you could always get married! Might also help.

*Or maybe other European ancestors.