@Rashim Sharma your biggest challenge will actually be finding a lender.There are two banks that have offices in USA and Detroit that often will lend to Canadians buying in the USA.Can refer you to a Tax Attorney here is the US that has hundreds of Canadian clients with US properties:)

Challenges?

NIMBY syndrome is perhaps one of the largest challenges any sober house will face. 

I have previously completed a fix-and-flip project, which, despite a few challenges, was successfully sold within 30 days of listing on the MLS.

@Erica Wilson challenges with LLCs:1) Setting it up correctly.

Not to say buying an existing property doesn't have its own challenges, but development is just different. 

Preferrably, stay in the same area and continue to learn.Going to another area would bring additional challenges that you may have difficulties meeting.

., but financing can be a bit of a challenge.

If you've never renovated anything, it's silly to think you can just buy a home, flip it, and do well in this environment.

I also make sure we get on the same page by writing down our roles, responsibilities, and even how we’ll handle potential challenges or surprises.