This is a house that has additional square ft added on, so they listed that as the reason for marking the question as positive, as new foundation and support was added for the additional sqft.My question is: Is it a standard practice to check this box as "yes" in the disclosure when additional square feet has been added on to the property?

I would talk to a lender, they look at your Schedule E section of your tax returns and add back depreciation, so basically, as long as that number is greater than the mortgage, your property will be a net zero on your debt to income ratio or it will be at a positive best case and small negative worst case, so you only have to really qualify for the next property. 

The majority of my investing is out of state as the cash flow opportunities seem easier to attain (at least in my position). 

Estate investment, what's my current primary residence in Knoxville, TN.

After a few years, you would start to see positive cash flow. 

Hi Micah, HELOCs will only go up to 70% LTV on investment properties, while for primary residences they go up to 90% LTV.

You'll take title, but it will be suject to (not to be confused with the popular purchase method) the superior lien position.

Last year, a few months after purchasing my primary residence, I took the leap and bought my first flip.While leverage knowledge from books, podcasts, talking to peers at meetups, Facebook groups, I connected with a great contractor, real estate agents, and subcontractors.

You have no positive cash flow, no upside equity, and virtually no downpayment after closing costs. 

In this way, I could eventually come to a position where it is possible to "self-finance" every new property I buy, and become self sufficient with regard to financing -- This, and still maintain exponential growth.