At the closing table of the cash out refinance (he needs to have a MASSIVE amount of trust in you, too), you could voluntarily quitclaim off title, leaving him as the sole owner, with the mortgage in his name, with you having been paid, and we all live happily ever after.... after a VERY HIGH RISK transaction that took >6 months and required MASSIVE amounts of trust all around.

. - Certificate of occupancy—Sale or conveyance of title.If the inspection reveals violations of the City Code, excluding "life-safety" violations, as determined in the sole discretion of the code enforcement department, the subject property may be issued a "temporary certificate of occupancy" to permit the property owner to remediate said violations while occupying the property.

Being a salesman and the sole provider for my family, the stress of constantly performing is pretty high.  

Also if you think house hacking is the way to go, then how, if you were in my shoes would you proceed with doing so.

A business can be a sole proprietor, partnership, LLC, corporation, etc.

My Response: I think dedicating the next 20-years of my working career solely to a company and expecting them to take care of me in my retirement is far more risky.I constantly have to remind them that we've had these same conversations over the past 10 years (And 3 cash-flowing Buy and holds to date!)

Also, the renovations I did on the house were so extensive that any attempt to segregate the appreciation and costs, solely related to the underpinning and 8' basement ceiling height, would be speculation.

@Miles Curtis - Just to add, my CPA would charge around $200-225 for someone in your shoes.

I have a partner and I can't add him to the business as a sole proprietor.

If an investor buys the house from the wholesaler, he steps into the shoes of the wholesaler and takes over the contract.