Any insight would be greatly appreciated as we navigate some new waters!

You might need to talk to a good CPA to navigate this.

Real estate is NOT VERY RISKY and people who think it is, are generally under-informed about the process and how to navigate the system.

I figured people might wake up at night in a strange house and might need the flashlight to navigate. 

You have a couple of issues to navigate.  

We are rigorously paying off student loans and expect to be done in about a year from now (April 2019, is our goal).

it made me navigate further through the pages and now I'm learning so much more.

Is it cost-effective to have a RE attorney draw up the contract/paperwork to protect my interests, and kinda help me navigate? 

When I have to adjust this on Airbnb it takes some time to navigate to the menu where this is buried. 

I'm trying to help a friend navigate a creative loan to buy his current rental house and capture some 'free equity' while keeping the stability in his son's life that he has worked so hard for.Brief backstory:  I've known the guy since middle school, never really close friends, but we've stayed in touch through Facebook over the years.