If this property is hard to rent, or is functionally obsolescent (only 1 bathroom, no yard, etc), or has deferred maintenance that will be costly, or is in a location that is not appealing to Tenants, then maybe a sale would be a good option in favor of a property that has better Tenant appeal, which will likely increase rent and avoid long vacancies in between Tenants.An option to consider....

•If your real estate broker’s license allows you to handle evictions, advertising low-cost eviction services can be one of the best lead generators.

There are no upfront costs so why not establish a relationship with someone who actively represents real estate investors and move forward with vetting your ideas.Best.

Pretty reasonable cost too. 

I wondering if I can deduct any of the repair, closing cost and deprecation on taxes. 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

Seems like it's in a lower end area so if it is filled you will have tenant issues and turnover cost.

I am trying to get a good hang of the rehab costs since I’m new to the are (from Dallas).

The property offered a balanced investment opportunity—enough to significantly enhance its value through renovations, yet manageable in scope and cost.