So to achieve the dream of having a paper loss from real estate it seems necessary to be pretty highly levered and/or operating in more A class areas where your cashflow is lower relative to depreciation and interest.

The contractor can achieve his equity based on an agreed upon "cost" of his time and materials.

Goal achieved.

Or can super returns be achieved with just as little head ache in great areas... ?

If your goals are sales and or investing, I would align with the right Brokerage that allows you to achieve your goals while they take care of the onboarding, training, technology, liability and everything else that comes with running a Brokerage.  

The questions and pointers you provided helped steer the conversation in the direction I was hoping to achieve. 

The unit I recently purchased will rent for $2,000 - 2,200 mo. and I plan on living in it for 1 year so was able to get the lowest rate as owner occupied (max 2 at a time) so that helped lower my monthly PI payment to achieve more cash flow.

as far as im concerned, i don't own much until this degree of ownership is achieved.

My Why -  I want to get out of the rat race and achieve financial freedom in the next 10 years so that I can travel with my wife and play guitar all day!  

And if I'm shut down, I'm still on the hook for the duration of the lease- I can cover and qualify for it, but it's important that I achieve the financial goal I set out to do.