When people make the irrational choice of buying a home with an economic cost, that does not change the home into a liability, it means they made a sub optimal investing choice, like buying Lehman Bros in '07. 

Those people should be like minded, and be able to help you and your strategy achieve your goal.

@Cayman Rigdon I would further verify the location and the achievable market rent, talk to at least 2 reliable property managers.  

Timeline to achieve this is 10 to 15 years,  conservatively.

This will defer all of the tax liabilities.Parts of the tax code can be combined to achieve this, but 1031 is the simplest, most straightforward, and can be conducted by any investor (read: accredited status not required.)

Any bulk discounts you could hope to achieve are outweighed simply by having the word "Commerical" in the policy.  

I'm very much a fan of learning by doing - but definitely have forwarded my career quite a bit by achieving a few different certifications.

The IRA is the borrower when the refinance step is achieved.  

Everyone knows that if you leave any money in the property, you are underutilizing your capital and thereby losing out on the almost certain gains you will achieve from leverage.

Together we agreed on a brief yet realistic scope of work to achieve that ARV for this particular flip.