If the price point is feasible I'd advise to do your first flip locally that way you can build systems and processes and gain the experience of doing a flip while being able to monitor close by.

Need to put processes in place even with property management.

It's typically a double skip process, first to skip trace the registered owner/manager/agent of the LLC or trustee of the trust.

I'm in the process of trying to find a lender either in the US or Canada that will work with Canadian buyers which will allow me to take on bigger projects and reduce my own capital investment.

I have been in the process of learning how to run the numbers myself as well as with help with very experienced agents on my team who have worked with many many investors. 

Hello,I am in the closing process on my first rental property duplex.

And getting anything done with the city is a painfully slow process lately. 

Or do I need to change the structure of my LLC and put the contractors I hire as employees? 

Have you (or anyone else) seen a municipality where they had a permit process allowing non-owner occupied STRs, then they changed course, prohibited STRs and did not grandfather in existing licences?

That would give you a chance to experience the home buying process, the rehab process, and get educated without getting over your ski's.