The key is to do the calculation for the profit margin.Even though, IMO for a metro city like Chicago with a high population, the majority return is from using the leverage to increase the equity + appreciation.

Check out the video below from Low VA Rates on how you can calculate your remaining entitlement.

I'm wondering if I'm using the calculator right.

I would really like the hard data broken down by property so I could calculate trendlines and regressions based on property classifications and features.Any help would be apprecaited!

Are you calculating based on purchase price?

Likewise, I also purchase my house-hacked house in New Brunswick and I calculated that it will cash flow $1,100+ once I leave the place.

You should definitely get the pro membership, it is so helpful using the calculators and the BP Insights that they now offer. 

if so, calculate how much it cash flows, add to that the new property cash flow, how does it look compared to if you sell?

So after using the Fix and Flip calculator for the first time I realized the calculator asked the purchase price, associated costs and desired profit; however at no point did it ask for my expected tax rate.

Even if you just go with a square footage calculation, it's better than "thousands".