10-99 and TN Visa Need Help

Hello everyone, I am a newbie, I have a few questions regarding TN and 1099:

I am Canadian. A friend of mine just started a LLC in New York and he want to bring me on board. His LLC is solely comprised of himself at this moment

and doesn't have any Canadian offices. BTW let us not worry about tax at this moment, I will sort that out later.

Question 1:
Can I work at his LLC as a 1099 employee under TN Visa? (I am a statistician)

Question 2:
What is the necessary paper work for him and for me?

Question 3:
Do any of you know any reputable lawyer based in Toronto that specialize in this area of work?

Thank you for your time.