My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

Search the archives; plenty of content on the forum on sober living operations.

I have added pre-payment penalties on my refinance loans to decrease my rate substantially. 

So after being laid off a few times in the last 8 years I decided to get back into investing but this time focusing on buy and hold multi family real estate so that I could built wealth that could help me retire my wife who just had a long battle with cancer and survived , but is now back to work, and I want to give her a relaxing life free of all the stress of the world (by the way did I mention she is also in the mortgage lending field) so that explains the urgency to retire her from w-2 work ! 

Finding out that s corp was not the route based on everyones input ive seen.

@Nathaniel Kamp This sounds like an opportunity worth exploring, but time is not on your side here!

@Chris SeveneyI ordered one report on https://www.neighborhoodscout.com to check it out .

You should never pick your 1031 Exchange Qualified Intermediary based solely on their 1031 Exchange fees, costs and charges or the size of the institution.

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

As a beginner, you can learn a lot from your uncle with a few rentals in another state or a co-worker who's on their second house hack.