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

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.

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?

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.

(best known for his tenure as chairman and CEO of IBM from 1993 until 2002, wherein he led the company through a great turnaround).

This could be a great opportunity for you to meet a ton of other investors and companies that help investors in many different ways.

Multiple, billion dollar companies are investing heavy in our area, such as Intel, Google, and Amazon.