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. 

I have helped thousands of RE investors clients get business credit for RE investing since it's a great option for people looking to get started in RE, it's also great supplement for the seasoned investor looking to do more deals.

While I use Evolve and they send their emails for checkin, I supplement theirs with my own Mailchimp campaigns that provides further info on their stay at my propertyies  All of this is powered by an automation engine I built using a free service called Automate.io that leverages my Google calendar to send tailored emails to my guests throughout their stay and automatically notifies my housekeeper of new and updated bookings.At this point, barring a broken toilet or something, I only have to spend about 4 minutes on each of my bookings