That said, targeting homes needing work or properties sitting unsold due to poor pricing can still yield opportunities—that's what I do successfully.

He created it for himself originally,  and it became a success afterwards. 

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.

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