You can achieve those returns investing passively in real estate (syndications, NNN). 

I would be more than happy to assist you towards achieving your investment goals.

@Victor Chen it really depends how you use it, you could achieve pretty much the same results going in unrepresented instead of becoming an agent.

Although I am planning to continue working within Education as well, it has become glaringly clear to me that rental property investing may be the best tool/skill around that can help me achieve financial freedom.

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.