This person would essentially be instrumental in putting the entire deal together.Given the significant role this individual would play, I'm curious about how their involvement is typically reflected in the closing documents, if at all.

My entire down payment has easily been returned to me in cash flow, and I have plenty of equity in it. 

When you rent it out the insurance won't cover for possible loss.

Is it possible to sell these properties/ LLC interests to 3rd party and have the QOF benefits transfer to them?

My strategy with this is to build equity as quick as possible so that I can apply for a HELOC, Home Equity Loan, or do a cash-out refi to buy my second property (investment property) if rates end up falling in the future.

It will create moisture and mildew and open you to issues including possible lawsuits....So my advice is - don't do anything until this is no longer an issue....

Their lease agreement expires in 11 months.what is the best approach to motivate the tenants to address these two issues and be as civil as possible about the situation?

I have also read "Rich Dad Poor Dad" and "The Book on Rental Property Investing", both are tremendous for wrapping your head around the possibilities to achieve financial freedom and how exceptional real estate is as one of those vessels.

It was possible for a resident to view a property, be approved, sign a lease, and move-in without ever talking to or meeting a human affiliated with the owner or property manager.

I don't think you need to be capable of setting up and customizing an entire accounting system to be a real estate investor. ...Go with something that's already configured out of the box for real estate investors (buildium, stessa, Digb) & get a CPA to help you with taxes.