This is causing absolute chaos for me now with my insurance company. 

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.

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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.

We run all this through a larger software but before we owned a management company we used Trans Union. - Verified income must be a minimum of 3X the rent. - Current employer reference must be provided and we must speak with the employer.

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

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.

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

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