He's an experienced investor who's delivering the truth learnt (painfully) through the school of hard knocks. 

Roofing is one of the key jobs in this business, and the more you know about it yourself from a hands-on perspective, the more respect you're going to get from roofers, who tend to be the most clannish and arrogant of tradesmen because they do the most dangerous residential trade, although the actual work itself isn't typically as complicated as more highly paid trades like plumbers and electricians.

If possible, we do not want to exacerbate this (of course if issues arise, we aren't afraid to evict/do cash for keys, but we want to at least try to make it work first). 

The key is to find properties that needs rehab and also more doors onto the property. 

The key is, knowing what you're doing.

The trust is the key necessity that allows the legal transfer.

The key is moving out early so you have time to make corrections if needed. 

You could make it a condition of the sale that the property be delivered vacant and in the same condition that it is now.

We all know persistence is key but what is working for you today?

Below are a few more thoughts on pros/cons.Pros: If you're new to real estate in general, you'll learn the mechanics of RE transactions, the governing laws and the key participants and services that support a transaction.You will interact with other realtors that may help accelerate your understanding of the market values and dynamics you're working in.