So in what you've learned, do most people not leverage their self-directed IRAs for income generating properties?

I have also found that joining a local or fairly local real estate investors association (REIA) is a great way to learn localized operating information.

I don’t know necessarily how I should approach him about the potential his equity has to change the dynamic/financial freedom of our family for generations to come.

With only 1 or 1.5 bathrooms, there is also less mechanical things to go wrong which gives you a lower cost of operation vs. houses with more bathrooms.

The properties are for long term hold for cash-flow generation. 

That type of sizable deduction could help whittle down a large tax bill.https://www.investopedia.com/articles/07/oil-tax-break.aspIf anyone has experience participating in this type of investment or knows well-known and respected operators in this space that put together limited partnerships and private placements, please share that info here. 

If it is not generated by the property it is not true cash flow.

Do you know approximately what your operating expenses would be?

I mainly operate around Philadelphia and Bucks County (grew up in Newtown). 

Buy a nice property- maybe even pay up a bit for a lower cap rate, and demonstrate to him the steady income you've begun to generate with your capital(and hopefully a lack of problems with tenants as well.)