I currently work a standard “day job” in an office (actually located in Wilmington, DE), however my goal is to begin to generate and build my wealth in other avenues outside a typical paycheck and become more financially independent/free.

Both homes are generating income now but for a long time we were just paying mortgages getting them updated... it was like we knew we wanted to get them onto the market but we were so busy as Realtors and U was home schooling out four kids... we dragged our feet.

I use no interest for a year credit card loans all the time for rehabs or random things that cost under 15k.

What are some good programs for CRM, lead generation, marketing and advertising?

I can schedule a meeting with my CPA at just about anytime (without all those extra nitpicking fees) and throughout an hour call we'll just discuss random laws, taxes, experiences, etc for half the time while still making sure business is discussed and we take care of what's needed. 

Also, hopefully you've been keeping bank statements to consider this an income generational property.

After 2 years, however, the property would be fully paid off and would start to generate a profit.

My current portfolio consists of 10 Short-term rentals and 10 long-term rentals that generate $40k a month in gross rent and about $20k in net profit (roughly half).  

Is there a way that I could help him generate enough cash flow to start paying off these debts?

Service based retail that is hard to replicate online, such as convenience stores, restaurants, QSR, grocery, wireless stores, dry cleaners, medical offices, hair and nail salons, etc can generate strong risk-adjusted yield compared to apartments.