Geez, there’s so much opinion, emotions, beliefs, and personal experience in this thread.  

Since you've stayed there and the lot is open, I see the lure, but any time I see something like this - "This is a pure emotional type of investment and I want to honor it."

He is securing expensive debt, not debt through a bank, isn't putting any capital into the deal and structuring the equity investment in a highly risky manner without any upside offered to the investor.

To stay secure, I’d recommend saving 3-6 months of mortgage payments, budgeting for repairs, and possibly investing in a home warranty.

Agree with @Jeff Pollack on having the guts to leave the security of a JOB.

You have engaged and paid securities attorney and are compliant with Reg D offering 

Also travelled 2 hours to find a security door design I saw in Orange Walk. 

Depending on the application, first, last, security, and another month or two.

In the lease it states that a security deposit of 1 months rent was collected. 

Luckily, I did not include this unit in my underwriting when purchasing, so the survival of this property is not contingent on this situation.Continuing to optimize for management of the building when I move out, like moving everyone to online rent payments or adding remote accessible security cameras.Exploring opportunities to expand my portfolio—I've begun my hunt for my next 3 to 4-unit building to house hack, ideally in Lake View, North Center, or Ravenswood.This year taught me that real estate investing isn’t easy, but it’s undoubtedly worth it.