I'm considering partnering with a non-profit that would manage the sober-living program; with me just providing the house passively for rent on a per bed basis. 

There is a cumbersome way to do it on paper forms, but you should not.The only sensible way is to submit your 1099s to the IRS online, however not directly with the IRS.

I agree that working with people is easier and more cost effective than the alternative.As I read this, I'm considering creating a Cash For Keys written program that I can give my tenants at lease signing to remind them to come to me rather than just stop paying. 

That is online with what we’ve been paying when we were able to find help.

After graduating in 2015, we moved to Oahu, where she completed a one-year AEGD program.

The LP got it from a friend who is in some kind of real estate mentoring program.

@Jorge Vazquez we stopped doing signs over 10 years ago.We had a separate phone number on our signs, so were able to track traffic & applications from them.We were getting more & BETTER leads from our online ads then the signs - so an easy choice to stop using them (also time & money savings).

However, aside from that, I couldn’t find much information about them, and the only online presence seems to be the wife’s LinkedIn profile (though I’ve never met her in person and am just going off her profile picture on Zillow).After submitting the application through Zillow, we attached our income (two months of pay stubs for each of us from our current jobs), work references, credit and criminal background, rental history, and the contact info for our current landlord (who just so happens to be my fiancé’s father).

I was seeing information online that suggested both routes...Thanks in advance for the help!

Start small, be patient, and stay connected with local meetups and online investor communities for support.