Is he buying it from you or is it a gift? 

I contacted an attorney's office in Wyoming to set up the LLC and they told me:"A Wyoming LLC will not provide a GA piece of investment property with any asset protection.

First 10 years I/O and fully amortized for 20 years thereafter..If it's full income verification, strong credit and a lower LTV you should be able to get there with a mild buy down..Check in with @Joseph Chiofalo for a quick second look.

In this type of scenario, is it still worth buying the duplex with one unit owner occupied?

I have a deal all signed to buy a home sub2 in Pueblo Colorado, but I realized the mortgage is a FHA loan.

OLD stock yazoo clay and houses that originally were built as cheap as you can build .. of course not all but a vast majority of what you folks buy for cash flow rentals.then  on top of that a VERY tough tenant base and that market can really frustrate folks I owned over 200 of those and the happiest day of my life was when my partners bought me out for 4k a door.. done gone and good luck lOL

For context, I do have a decent grasp on the real estate market and financing as I have been a mortgage loan officer for 4 years now.

I think it works for a great buy and hold rental situation, but it is probably a class C neighborhood and you will need to put a lot of money to rehab a 1950's property to get it rent ready.

Would it be possible for me and him to buy a new primary residence for him to live in, while we rent the house he is currently in.

Looking at buying an investment property in Jacksonville, Florida from JWB Real Estate Capital.