I would give your PM the benefit of the doubt so long as they explain.

@Logan Eckstein Discuss the benefits of selling a property with your company (over others).

It sounds like you’ve done that somewhat and you’ve considered all the side benefits.

However after crunching some quick numbers, I’m trying to understand the benefit of a cash out refi vs just getting a conventional mortgage.

So who benefit in this?

The positive for the client, he says, is that there is no padding of these fees (though there could be a kickback to the contractor) but I think he also has a cash flow problem and the benefit to him is he doesn't have to front the money, which may not be atypical in this business.My concern currently is around equipment rental.

At this point you'll probably have a LLC because there's no benefit to keeping anything in your personal name since you won't get better financing terms as a result. 

The benefit of this is that I get to decide what is accidental damage, not an insurance company.It is a much better process (in my opinion) than having to withhold money from a security deposit, which never makes a guest happy even if they take responsibility for the damage. 

But I've always believed in the value of a mentor - someone experienced in the industry from whom you can learn through osmosis.Having the benefit of working in this industry professionally, I've participated in the acquisition/disposition of over $1.0B+ of commercial assets - multifamily, retail, industrial and land.

And think of the benefit to you in this scenario - You have your 1031 replacement ready to go.