I think you need to put some more meat on this bone by letting us and him/her know exactly what you are trying to accomplish and what your approach looks like; we are otherwise shooting in the dark with where to direct you.

Leave a little meat on the bone, but not too much.  

He is in his mid 50's and is convinced he will be working to the bone until he dies.

Who cares if it was "a deal" that left meat on the bone to pay a middleman?  

Then the fun begins, bone up on cost accounting, allocate expenses to each department for fixed costs and variable costs.....better yet, see your accountant.

I could ask a hundred questions before giving you an answer......so, throw us a bone here, what is going on?

I've been assuming this is an investor cashing in on equity captured through purchasing in 2009-2011 but leaving meat on the bone for another investor.

People on some of these "extreme early retirement" blogs do a disservice to people that visit the site because they know very little about investing and preach cutting expenses to the bone to achieve financial independence sooner.  

I'm looking to fix and flip cosmetic homes bringing the old into the new, but the bones of the house are in excellent shape.

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