If you want to play a passive role, a real estate syndication or debt fund could be a great way to go.

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

Then figure aprox what your refi numbers/value would be given those rents/expenses at a stabilized point,  and that to me is your "all in" - From there it becomes an exercise of what it will take to get to that point or property condition?

So there it is, no exercising eminent domain for a quarter trillion dollars.

Currently I'm looking for some kind of methodology, software or app, that I can use to manage the properties, which will allow for another family member to step in to my role relatively seamlessly if I were to pass in the future.

Networking plays a crucial role in this industry and remember to keep learning continuously.

He's an investor himself and recently left his role as partner at the largest firm in the area to start his own company.

Quote from @Eliott Elias: Its role in real estate is too hyped.

Do number, size, or area of investments owned play the biggest role in that decision? 

Learn from the exercise and do better on the next.Good luck!