My 0.88% rule on paper has turned into losing $300 to $700 a month with repairs called in by tenant on Class C#1.  

Seller will lose time on market, time value of money, etc.  

My wife's fear was that something would go wrong and I would lose everything. 

A lot of coaches (if they're good) should be able to shorten the learning curve for you individually, by understanding precisely where you're at and tailoring a plan for you... but ultimately, I wouldn't lose sight of the fact that you'll still have to put in the time and get your own first-hand experience with it - that's where the real, tangible learning happens.

Does he share the risk of losing money?

I just dont come in to lose.

"I too was in foreclosure years ago so I know what your going through"  that is a very common so when folks losing the home see the same pitch multiple times they know its just BS. 

The key takeaways for me, because they aren't the most obvious, are the benefits of front end loaded amortization but also important to realize that the seller will lose their future eligibility (in the case of VA).  

If they cause damage to the flooring, then they are definitely losing the deposit.

You will lose money to inherent issues that plague lower income populations.