If he wants to have total control over his retirement funds instead of going through a middle man for every investment and every transaction then he may want to explore Checkbook IRA. 

You make your money when you buy...you realize your profit when you exercise your exit strategy down the road.If you do anything now, rationalizing on future events you have no control over, that will recover your loss (overpay) at purchase, you lose.  

Amil, here is what i have done in the past with LLCs and partners.There was one main operating llc that i controlled since i was the leader on the endeavor.

and I commend you on how you portrayed your scenario, as we all should take responsibility and take charge of what we can control.

when you wholesale a deal to a wholesaler who is finding the end buyer, you've lost control of that end buyer.

Remember you don't have to own a property to control it.

The bank has no control over the AMC's fees either.

And especially in SF, with rent control and urban density, you literally get extreme and absurd situations like a multi million dollar condo literally RIGHT NEXT DOOR to a rent controlled flat where the immigrant inhabitants (6 in a small 2BR) collect recyclables in their back yard.  

Remember you don't have to own a property to control it.

Remember you don't have to own a property to control it.Download BP’s newest book here some good due diligence in Chapter 10.