I am doing everything at the same time....After one deal and I will automate it all and outsource the work.

I don't think outsourcing all of the thinking is the way to go either. 

Im just now implementing systems to systemize and outsource some task.

Some roles can be outsourced.

I'll also take the property manager advice to heart, I'm going to need someone who can look after my rental any time I leave the area and would eventually like to take a cut on income to outsource some of the work to a manager.Speaking hypothetically, do you think it would be better to buy a $50,000 home that rents for $650 vs a $25,000 home that rents for $450 because of fewer tenant issues?

My dream is to build a buisness where I can eventually outsource most of the day-to-day tasks and generate a passive income stream that allows me to stop trading time for money.My situation is this: my parents bought the house I grew up in from my grandparents, with a family discount, and are interested in keeping it in the family going forward.

(or better yet, outsource & use a VA at www. upwork.com to do the "office duties."

Several people outsource this responsibility, but it is still crucial to hit your budgets and projected turnarounds. 

This can be outsourced.

Finish Basement, Add Full Bath, Section 8 RenterAssume $20,000 in rehab to get into rentable condition.Note that the Cash Flow and ROI numbers reflect both the scenario where we outsource the property management and where we do the property management ourselves.