I believe subject to transactions, done CORRECTLY, between KNOWLEDGABLE participants, with FULL DISCLOSURE, are typically successful transactions that have benefits for both sides.  

My advice would be is to talk to multiple investors who have real world, actual success-based experience in flipping over a sustained period.

Personally, I've had success in Linden, Southern Orchards, South of Main, Driving Park, and Franklinton to name a few neighborhoods in Columbus. 

I faced numerous hurdles and stressful moments, but I persevered and built a successful approach.To tackle this challenge, I recommend starting early by building relationships and seeking investors.

We see a lot of our clients in Denver and Colorado Springs have success with either rent-by-the-room or some sort of basement apartment/ADU setup.

But I wouldn't worry as long as your filings said successful.  

His goal is to diversity his money as he's been very successful in another business.

If you're expecting property owners to sell their home to you at a discount, you'll need to earn their trust - whether that be by demonstrating a successful track record with purchasing/selling similar deals OR by meeting them face to face and separating yourself from the dozens of local investors and realtors.Lastly, I'd recommend searching past posts related to this topic as well as checking out books related to your target investment strategies.All the best!

Trade some comfort for financial stability.Part of attaining financial success is being simultaneously optimistic and paranoid. 

You do that and success will be inevitable.