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

There was a tornado in Slidell, LA and I would like to know how to offer my rental house to the insurance companies so that I can house some of their victims. 

I have hit many of my work goals since starting my company in 2018, but I’ve missed out on a lot of sleep and gained nearly 50 lbs of fat by not exercising regularly and eating right.

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

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. 

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).