With some additions, this would qualify for the OMG category, but I think they didn't have that category back then when it was on the market.

If we sense there is a red flag, were asking them to upload additional documents like tax returns w2's etc.

Perhaps you could consider hard money in addition to private money?

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. 

It’s part of the qualification criteria, and any problematic tenant should be revealed by speaking with two or three prior landlords.

An emergency fund needs to be liquid, and immediately available to you in addition to being low risk and protecting principle. 

In addition to having cashflow to add value and push equity, I still have had decent appreciation.

Man, just in 3 years if you have the tenant leave every time, even without the negative cashflow, that alone can cost you an additional 20 or 30k.

Do you have additional capital to add?

Additionally, have a clear budget, factoring in potential repair costs, and ensure you understand the rules about earnest money deposits and closing deadlines.LLC for Real Estate Investing: Forming an LLC for rental properties can offer liability protection and may provide tax advantages, though the tax benefits are non-existence for rentals.