As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

I’d also prioritize getting pre-approved, securing financing, and starting small to build experience and momentum.Good luck!

We've secured many tenants who didn't know that we were actually the perfect match for them when they started their search.

From screening to security deposits to eviction, recent laws create many ways for owners to trip and fall.And now Multnomah County has prevented landlords from evicting delinquent tenants.

I'm a very analytical person who won't start a new venture without first gaining a solid understanding, establishing the right framework and connections, and ensuring that I'm securing a great deal.

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.

It's better to pay more, knowing you have something secured versus cheaping out and not even closing. 

But after an exchange - sign the purchase documents with one pen and pick up another pen to sign the refi docs :)Another strategy you could consider is reinvesting into multiple properties, where you purchase the first property cash (ensures some security and concentrates the equity) and the second property with a mortgage.

For added security, consider umbrella insurance alongside the LLC. 

Quote from @Stetson Oates: The vast majority of disputes are over security deposits and the most a landlord could lose is 3x the deposit amount.Slip-and-fall or other major lawsuits almost never happen.