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

He isn't rich enough to have a body guard and a security professional.

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

It seems like offering this as a separate package once you secured the booking is a good idea. 

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

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.

Look for undervalued properties.Network: Connect with local real estate agents, contractors, and other investors for insights and deals.Analyze Properties: Use the 1% rule to evaluate potential properties (monthly rent should be at least 1% of the total investment).Secure Financing: Explore different financing options like conventional loans, hard money loans, or private lenders.As for timing, if you can handle the extra responsibility, starting now could give you a head start.

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

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

The state doesn’t have rent control laws, but landlords are prohibited from collecting more than one month’s rent for security deposits.