She didn't want to take his fresh college graduate seriously, but I was young, dumb and hungry and didn't know any better and it turned into the best client relationship I have.

Although it was his to begin with so I don't understand that.The home is is great shape besides the roof, the slight leak in the A/C, indoor paint, and the kitchen laminate  floors bubbling up due to a fridge leaking but nothing serious. 

Based on verbal condition description of the property I estimated a ball park of $15K for repairs (seller claims it just paint and flooring but you know how that goes).

I was in a similar situation, where we bought a house for $5K, turned out to be a POS,  and I just flipped it on CL for $10K.. if I was smarter, I would have done the painting and put in appliances and sold it for $20K! 

One was for needing to be painted. 

Paint that thing. 

I'm in Ohio and we just legalized it so this is a fresh slate state!

In the last couple years over $100,000 has been spent to re side all buildings,there’s brand new parking lots,new windows, new hot water heater’s,new paint and new carpet.

It exposes some very questionable tactics in your business model (if you can call it that), and bragging about almost ripping off an elderly widower through the unlicensed practice of real estate does not paint you in a positive or professional light. 

I don't necessarily "need" the cash that's tied up in it but that is a big chunk of money I could potentially invest elsewhere (but without a known rate of return like I'd get on this place).The property is 2 hours from where I live so I need to find a property manager.Interested in any and all perspectives on this and happy to answer additional questions if they help paint the picture.