Assuming I'm a Canadian resident for tax purposes, to buy US property would it be better to incorporate in US, incorporate in Canada or avoid investing in US all together and why?

One option is to incorporate into Delaware or Nevada, who do have SLLC case law.

Once we have a tenant in, we make sure to get reviews from each and find ways to incorporate into the marketing, and consistently make sure that our MTR tenants are satisfied and any reasonable needs are met.

The Builders Risk will cover the existing structure at Actual Cash Value (depreciated value) and will cover the renovations as they are incorporated. 

I am not incorporated yet. 

I get the idea, just trying to incorporate it into my setup, which is 1 holding llc, 1 property llc which house 2 properties.Both holding and property llc have a separate bank account.

Would love to hear alternate ideas that we can incorporate in our property. 

I guess what I am trying to reconcile for myself is if this property is located in incorporated Cook County City of Chicago why would the appraiser list it as a legal bedroom if the City of Chicago would not or does not reconize it as a legal bedroom without having a closet?

Follow on question - is there a calculator that BP has that accounts for HELOC repayment or is there a way to hack the system to incorporate this?

There are different aspects of different types of engineering practices you have incorporated above but some of the broader strokes definitely find root in looking at things analytically and considering approaches from several angles prior to diving in.