You are missing a lot of steps and costs and forecasting of obstacles.I've been through the BRRRR 100+ times with clients. 

If you are a licensed contractor for instance and capable of major remodeling projects as your trade, this would be considered adding value to the property and would risk IRS action.Sounds like "improving" or "upgrading" the place is not allowed.

If you want to move the property quickly and ensure income, seller financing seems more practical despite the tax trade-offs.

I'm in a good position now and don't want to trade a career that is OK for something I don't like. 

As others have mentioned it is a trade off.  

The areas where I forecast the strongest future growth are Rogers Park, Albany Park and Portage Park.

He needs to be a manager, organizer, motivator, and educated in the trades and he has to give a you know what about the finished product of your job. 

They use our trade colors and trade designs.

Quote from @Dekota Oechsle: As someone getting started, what trade-offs are generally sought after for a seasoned investor to mentor someone? 

What's holding me back is that I am a risk manager by trade, so I tend to think in terms of mitigating potential risks.