When in Due Diligence have a thorough inspection and get estimates for any work that is needed now and potentially in the next 3-5 years. don't forget about the tax benefits to doing the work upfront.

He's also the developer and this is the first house in Phase II of this development.

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

That self-sufficiency test is sometimes the killer on 3-4 units, but the conventional 5% down option has benefits too and that's how I got into my first multi-unit househack.  

Ultimately, I do think S8 requires scale and lots of efficiencies but has its benefits. 

I'm trying to give them the benefit of doubt that he just DIDN'T know.

Are there benefits of joining a specific brokerage or are they all about the same?

When investing with them you get almost no tax benefits and usually get crappy management. 

Live-in-flip a four plex- live in one unit while you rent the others and benefit from the other 3 units paying a large chunk if not all of the mortgage.

And, factor in the depreciation and other tax benefits, deductions, home office, vehicle expenses, etc.