I'm looking to purchase a 2-4 unit in northern Illinois, the Freeport area seems to have tons of affordable inventory.

He's the CEO of a company that builds healthcare facilities, and you rented him a "fully furnished luxury executive rental," but then you said he's broke and couldn't afford to give his kids Christmas presents?

They'll have to find a home they can afford, and then one that meets the guidelines (needs to be in good condition.) 

You don't give any indication of what you can afford, so it's hard to give you much more advice than that.When asking for directions, it helps to know where you are at and what mode of transportation you are using (foot, bicycle, Ford F-350, Porsche 911, etc.), and where you want to end up.

The cost of living in here is more affordable compared to other major metro areas.

. - Make sure you get a security deposit and perhaps do a surprise inspection of their current home.S8 requires an inspection (mostly health & safety) before approving a lease and then annually thereafter. - Not something most landlords taking care of their properties have to worry about.There are limits to clauses they allow in your lease.

It sounds like this might have been some sort of "creative financing" scenario where the buyer has $0 but is trying to cobble together 3 liens and 8 JV partners to buy something they cant afford.

Sometimes, it’s all about finding the right nearby areas that balance cash flow with future appreciation to achieve your goals.Here are a few cities (there are more) just outside Atlanta that have strong RTP ratios and more affordable entry points, I suggest looking into:East Point, GA College Park, GA Douglasville, GA Lithonia, GA If you’re interested in any of these areas, feel free to DM me!

I think a DST might afford more investment options and flexibility. 

We have a lot of investors that rent space  as Airbnb (limited to 400 units)  and room space to students from a local ministry school, as well as others looking for more affordable options.