My goals currently are to help him get to a state where he can live the life he desires.  

With a strong desire to learn, I’m focused on acquiring the skills needed to make strategic investments and build generational wealth through real estate.I’m is eager to dive into the fundamentals of the industry, from property evaluation to cash flow management, and is excited to learn from the experienced mentors and peers.Welcome to the community!

And you now know this, but never, ever, neglect to have a firm contract and SOW in place again.

Your thesis is basically rent low and accept less desirable tenants so I don't think that is the best thesis to base an investment off.

If you feel you are ready for this and have a desire to ignore advice that doesnt fit what you want to hear just go for it.

To thrive in real estate investing, you must maintain a firm grip on your finances.

If I were you, I’d consider chatting with a property management firm active in that area...SlateHouse Group’s name comes up in local investor circles now and then...just to get a sense of what rents are really doing on the ground.

Quote from @V.G Jason: I'd partner with a lawyer that can help put some contractual language on the downside of working with contractors and real estate agents.I'd also partner with a RE brokerage firm that clearly understands your goals. 

If the office is disorganized, their processes likely are, too.Other ConsiderationsExperience: Choose medium-sized firms—they balance resources and personal attention better than large or small firms.Fees: you cannot afford a discount property manager.

I was firmly denied and told, "we strictly do not allow short-term rentals, subletting, or anything similar".