They somehow convinced my tenant it would be livable during this and my insurance agent has said they can pay me half a month rent if he stays (which I will pass the savings along to him) and if he decides it’s not live able they will give me a full months rent so he doesn’t have to pay.

My husband has a friend he went to high school with who is a real estate agent.

That threshold should be discussed on a per property and per individual basis with an agent that is trustworthy, knowledgeable, and has your back.4.

What specific roles do brokers hold that agents should not? 

If possible, not use an agent, to lower commission owed expense (not sure if this is possible in Chicago, IL).

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

Found many of my listings in its data and the numbers were so far off what my listings actually did, that it kinda lost me as viewing it reputably.

Is there anyone that has any suggestions or any good leasing agents that can help lease my properties out and help me get them vacated.

Find a reputable real estate attorney.

You may learn the ropes without taking on undue danger by starting small.Make connections with experts, agents, and investors in the area for real estate.