Would you recommend anyone?! 

I would recommend targeting 30 day minimum rentals (Most associations are 90+), allowing 12+ rentals per year (most allow 1-3), and no in-person screening for tenants required.

Any recommendations are appreciated.

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

LOL Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

My Insurance Agent has strongly recommended that I put a Construction Agreement in place with my Contractor to shield me from liability, etc. 

I've found that there are markets that have a balance of decent cashflow and decent appreciation and that's the type of market I eventually decided to invest in.I'm not too familiar with the different markets down there but I'd highly recommend looking into Candor Realty. 

Others recommend tools like Stessa or Buildium to track actual costs and project future expenses. 

We've had a couple HVAC techs recharge the refrigerant and one recommended replacing the entire system.