I may explain that while I’d like to buy/finance/invest in his property, I need to earn a certain return on my invested capital for the given amount of risk, and if not able to earn the return on the subject deal than I will on the next deal.  

Over the years, we have built quite a network of agents that bring us quality off market properties in the areas that we desire.

I believed I was putting that hard-earned money into something secure.

We desire a certain level of autonomy and trust with our clients.

Never heard of a voucher tenant being responsible for maintenance and repairs, rental licensing fees, lead testing upkeep, cap ex, reserves, book keeping and tax prep......and even if you self manage, it takes up your time and should be treated as an expense because its taking away from your ability to earn income elsewhere. 

I don't invest in section 8 housing and also have no desire to so maybe I am biased.- I live in Raleigh, 10-50 unit complexes will be hard to come by unless you're okay paying a premium.

A coach makes sense if you are 23 and want to increase your skills enough to earn a living with the sport.

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

I was specifically interested in his 2nd plan which was "Building wealth through single-family homes" where he basically says you save enough to buy your first property along with enough for other fees and then you just keep saving the money you make from that property along with some money you save from your job and once you have enough money you buy your next property and then you basically just keep repeating that until you have your desired amount of properties.

Your first step is definitely learning about the markets you are interested in and figuring our what your desired end state / goal is that you are hoping to achieve through real estate.