I wanted to update this thread to explain how things turned out.  

Hello Justin, I recently became a real estate investor and can relate to your same though process explained in your post.

He explains later that he likes listening to ideas that don't match his own.  

Instead, I'd like to sell this property and take the proceeds and roll that into a rental that's closer to me and use whatever tax advantages I can to assist me.I'm confused with how the 1031 works and was hoping someone could explain to me how to "use" it.  

The legislation is intended (among other objectives) to prevent insiders and in the know investors from purchasing lots of near worthless start up shares in an IRA and having some of them grow tax free into tens or hundreds of millions (like Peter Thiel did with 1.7 million PayPal shares purchased in his IRA for only $1,700). 

Try to view this as objectively as possible, as if it's not you in the situation but your best friend Ryan.

Do he and I separately wire the amount and I explain the setup to the lender?

Unfortunately I have no experience and limited knowledge in this field so if you looking for me to explain I am sorry. 

Here’s my objective.

Does anyone potentially have any helpful videos or books that helps to explain?