I can't help on the mastermind front, but I did grow up in Central IL and can relate to the "something goes wrong with a property, now I'm spiraling, and this was all a terrible idea" feeling.

Study the PPM and offering materials....see how the projections meet the actual numbers and what went right or wrong. 

But where this goes wrong for people is with: 1) The numbers the entire deal is based upon. 

Here are a few common mistakes startups make when purchasing an investment property:They calculate expected annual gross income based on 100% occupancy rates.Poor property management results in tenant turnover.High vacancy rates cause lost rent.The local rental sector is experiencing a downturn.High maintenance or repair costs eat into profits.Getting rental rate wrong—either not charging enough or charging too much.Before selling your rental property, it’s crucial to determine the reasons for lost rental income.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

What about sending a wire to the wrong place.

Aside from that, seems like you’re using LLC for the wrong reasons and others have already pointed out the issues.

What can go wrong here?

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

Who is doing what and what to do if something goes wrong.