If your tenants have an enjoyable experience with you, as opposed to hating you, you will go far if you are self-managing.

We've gotten that advice from an old timer in the trades, but Chicago is notoriously know for lagging with issuing permits and performing inspections.  

@Alex CollinsAs mentioned by Jonathan Greene.If you're transitioning from nursing to full-time real estate investing, focus on house-hacking in high-demand areas like downtown Indianapolis, Carmel, or Greenwood, targeting short-term or mid-term rentals.

Are you planning on doing the maintenance your self?

I self-manage, but I understand that's not a practical option for most people.

Income Snowball, a system of investing in which a person can create self-sustaining passive income).

Property Management: Are you planning to self-manage or hire a property manager?

It's about self-management, however it's so much more than that.  

You can also sell them on sites like paperstac, debexpert or others as well as brokers like Mission Capital, Rams or Phoenix.Depending on quality of paper and interest rate will determine sales price - also I would say self servicing can have a negative impact on the sales price as the major players in the space are not fond of self servicing. 

Toby - getting your license for self representation of you're planning on doing a lot of deals is a good option.1) You have to hang your license with a broker unless you have a brokers license.