There are documents that normally third parties will ask you about your 'status'If you work with a property management company, theoretically, they are suppose to withhold money on your behalf which trigues you having to file a return.You may be required to file a 1040NR which is different than the 1040 form that Citizens / Residents file.

Contact the company that provided you with Title Insurance.

I want to go the HML route but I just cannot find a company willing to loan for under $50k and most cases $75k.

You're targeting that highly coveted group of 6-12 unit, independent (not a company) property owners.

You should be looking at Airbnb and VRBO and booking.com and possibly FlipKey to bring you people, not to be your insurance company

I personally would transfer it through a title company - costs about $150.

Obviously I’m in Canada so would need a property management company so that would add to the expenses, but I don’t know, something feels right about an investment like this.

If I only manage my holding company - no active PM role - does that help avoid filing/registering in NY?

Option 2 - you create a new holding company which owns your interest in We <3 Real Estate. 

We made a couple of detours, bought a couple of flips instead of another multi...but similar enough and I count it as a success.I lost focus in 2014 and went off doing 1000 different things..started a construction company and completely lost focus.