Speaking of electrical, I had about 6 service calls on a rental about the electric heat and AC ... they messed with the unit all kinds of ways but never fixed it.

I have slowly built a team of people who can make decent repairs and renovations at an affordable price.

@Rod JosephYour post states "Mortgage Expense" is that supposed to mean that monthly debt service is $2,600 or is that Mortgage + Insurance + Cap ex + Management + Repairs?

Be nice to your tenants by providing a quality product and service for the money they pay you.  

I need: contractors, plumbers, electricians, etcAlso: affordable shops for materials!

As a very new investor living in Chicago and currently working to save money to afford an investment property, am I better off not trying to invest in Chicago?

Tenants are customers, customer service is what keeps people and retention is customer service driven.Prompt service, prompt maintenance, Clean building, good looking exterior and ground maintenance.Give people pride in where they live and they will stay. 

So I'm in my first ever mortgage (house hack in Chicago) and my mortgage is being serviced by Chase.

Experienced as real estate developer in Texas, I think you need a full service developer or you can sell the land as-is.

In 6 years $40k of my student loans will be relieved with the Public Service Loan Forgiveness program (since the university is considered public sector) and during that time I can take advantage of a university-paid master's program (once I figure out which one will best suit my goals).