Obviously aware of the major costs to consider (down payment, insurance, closing costs, etc) but was looking for help on other costs to include during that evaluation.Rehab costs will be specific to each property but just wanted to make sure there wasn't anything major I was missing! 

Contact the company that provided you with Title Insurance.

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.

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.

It seems like you're going through an exciting change from just flipping houses to creating a successful real estate company.

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.

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

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.