I am trying to add to my team.

What prices of my team can be local to me and which would need to be there?

Good with Their CrewOn bigger jobs, a contractor is basically the team captain.

Cashflow, ability to build a team, landlord tenant laws, price to rent ratio etc.......were all factors in the decision making process almost a decade ago.Now,  I wonder why your approach is an either or view? 

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.

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

However, I am unsure on how to go about finding the proper handyman/maintenance guy/management team to help run any out-of-state investments I make.

@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'm in a team who does these deals and we have a team of "door knockers" who go back weekly till the auction, they file bankruptcy which only delays 3+/- months 100% chance that the lender will as that their mortgage is removed from the bankruptcy they file NOD yet again.   

Being out of state, I would suggest vetting your "team", meaning find an investor realtor, lender/s (hard $ / long term), property manager, contractors, etc.