@Jacob Dalton, I'm going to have to agree with Jonathan Klemm (sorry, couldn't tag you) & @Brie Schmidt -- you can definitely be a successful landlord in Chicago with the right team in place.  1000's of investors do it every day. 

My wife last year closed 28 million by herself NOT a team thats by herself..

My firm is mostly remote but some of my team and I are in Henderson, NV.

I have a team of two who do texting campaigns and one who does cold calls.

It wasnt an easy decision, but he’s now breathing easier with stronger cash reserves.Another thought: refinancing.

Always research local regulations before investing.The Importance of a Local Investment TeamA knowledgeable local team is essential for success.

You can even connect with local HR teams and offer small referral bonuses to get more bookings.

If it is a good business with a hard to finance issue, he'll work with the loan team to figure out how to lend to them.

I work in acquisitions for wholesale and come across deals sometimes so amazing it hurts me to see my disposition team sell them.

They often have different vendors introduce themselves so you can build your team and they often have a local member do a case study on one of their properties to share the ins, outs, ups, and downs of the investment.