Think of 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.

I live out in Oak Lawn, and am pretty familiar with the surrounding areas.

I'm getting ready to purchase my first multi-family rental property, and I'm considering snow removal and lawn care costs to ensure these costs are captured in the analysis, if needed.

Looks like they are competing with open-door / Zillow and other Ibuyers to artificially inflate the prices. 

It's the area where emotional intelligence excels over artificial intelligence.The cumulative result of these consumer preferences and algorithmic pricing is that the consumers willing to sell to Zillow were those with the least desirable homes.

I have never rented a house before and looking for mentorship on contracts, picking a property manager, tenant screening, what to include with the house (lawn & pest management...etc) and how to determine the best cash flow.

Will you have to do snow removal/lawn care?  

Typically in my area I would be responsible for lawn care and snow removal but due to several unique properties I only have lawn care at the duplex which I house hack and snow removal at the 4-plex which has a shared driveway and I provide the snow plowing and the gentleman who shared the driveway with me provides the lawn care.

Any great self-managed property needs a high-quality photographer, handyman, cleaning crew, along with other property vendors as necessary (pool care, lawn care, pest control, etc.)What tools can I use to automate tasks?

Even our local state college does it that way and by spring it is fertilizer for the lawn.