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

@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. 

Although she got very fortunate ( probably because of her skill and dedication) But the CFO of one of the spin offs on  brought her over and she is now the head of corporate finance for this company and will be getting all the perks that come along with it  pre IPO stock etc.

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

This requires a dedicated effort sourcing and analyzing hundreds of deals to find the one or two worth pursuing.  

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

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

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

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.

Hire a reliable co-host or property manager (15-25% of revenue), automate pricing and guest communication with tools like PriceLabs and Hospitable, and build a strong cleaning/maintenance team to handle turnovers and inspections.