I see myself slowly transitioning from full time rate race job in the next 5-10 years with real state supplementing other income.What are my next steps?

I suspect some of those landlords who aren't already listing with services like Homesuite, will move there as a way to supplement lost business.

Some grew up in real estate, some worked in construction which translated quite well to rehabbing, others came from a finance background and can feel comfortable working the numbers.I'd say hedge your bets and find a way to add/supplement what your currently doing with real estate.

Not having a job and supplemental income source or cash buffer torpedoes your pillar to negotiate.

Their is no reason to justify supplementing any tenants rent.Tell your tenant rent is rising to $550 in 60 days (assuming you are in a legal position to do so).

Currently I work in retail management in the supplement industry.

Place looks great @Brian Pulaski, congrats on the flip, hard work but works out to be a nice supplement. 20hrs / week for 5 months puts you at 400yrs, 40k profit get you $100/hr, not a bad part time job!

I am now thinking of getting my RE license to help supplement my marketing because I friends and family know I know what I am talking about so they ask me questions and then go buy from a realtor.

I have the required $50k downpayment in the bank, but I'd much rather pay $30k myself and supplement the $20k balance, which leaves me with $20k in the bank to fund another house. 

I would recommend that you utilize your father knowledge with his knowledge of the local market and use BP to supplement that knowledge.