Additionally, I'm working with the RE Ally Property management team, who was able to find a tenant to rent at slightly above market rates without any vacancy.

I was to start assembling a team together and am looking for any recommendations of contractors that will offer a little bit more hand-holding, as I am still fairly new to this process. 

I have a robust team of mortgage lenders, title companies and RE attorneys.

Then you'll need to build a team of contractors to handle renovations and to help with things such as property inspections.

And don’t forget to build a solid local team—agents, property managers, etc.

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.

@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. 

I have friends in each spot and think they could help me build a great team.

Best of luck building your team and making your investment work for you!

You either end up doing it all yourself or need someone on your team that can do it.