Otherwise, you can never attain financial freedom because rents will not outpace inflation.How long your rental income lasts depends on job growth in the investment city.Non-government jobs are inherently temporary.

If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

Depending where your rental is in Chicago, you should also be flexible with your requirements.

Depending on your goals, budget somewhere around $3k-$5k per room.

There is also a significant investment happening in the Buckeye area that should drive appreciation in that part of town in the coming years although currently I would classify that area more as a C- or D+ depending on the street.Best of luck to you!

More control over your living space.Cons: Significant upfront costs (down payment, closing fees), ongoing maintenance responsibility.The answer depends on your goals!

Both can save time and improve efficiency, depending on how hands-on you want to be. 

And good to know you have dependable contractor and realtor, that is a silver lining

*Eventually* they will come back, which might be in 2 years or 10 depending on how aggressive the tree and bushes are that are nearby.

Since they are 1099 independent contractors, payroll taxes are not paid by the brokerage so agents have to pay about 20-30% out of the portion of the commission they get to Uncle Sam for income taxes, depending on their tax bracket and individual tax situation of course.