. @ Nathan Eiland what you are describing is not house hacking, it is just buying an investment property.

The door could just be damaged due to under wear & tear although the way you described it’s not.

But based on how you described it most lenders can accommodate a refinance right away with no seasoning/waiting.

Did a 1031 exchange for a commercial building I owned for this Ocean View Short-Term Rental in York, Me What made you interested in investing in this type of deal?

If I don't have that and they want an update if they were accepted I tell them I have other viewings and to be fair to them am giving them a chance and have not made a decision yet. 

@Wesley Mullen,TL:DR- look at some differing viewpoints and make a decision that is best for and your family.Soap box ensues.I’ll give you what appears to be the sole dissenting view-the money in your 401(k) gets taxed as ordinary income when you withdraw it in retirement.

Personally if you trust your contractor and he knows what you want/like, I'd talk to him about what he'd want as compensation for viewing properties.

I was trying to describe what will be be a profit for me, after the loan is paid off. 

Try to get the 30,000 foot view before focusing in on wholesaling.

The current structure you described has a number of problems.