US investor taking on a Canadian partner

[Brian Barfoot]

Happy New Year everyone!

I am starting to get the ball rolling with my buy-and-hold investing (three SFRs operating, two more in process) and I have a friend from Canada who wants to join in. I have a lot of questions and we are willing to take things slowly so that everyone is protected as well as benefiting. He would eventually like to move across the border into upstate New York and he has a joint USbanking account with his US citizen fiancée already.

To start: Are there tax penalties that he would have to pay to invest across the border? Are there other headaches he would encounter? Are there headaches we will encounter creating an international partnership? I found it pleasantly easy to set up a partnership with someone in the same area but I know the imaginary line between the countries makes things different. Could he use the joint banking account to bypass any of this without breaking any laws?

As I said, I want to do things the right way and I feel like it could work well for both of us in the long run.