There are not a ton of comps on Zillow or other websites that I have checked and it was last sold a while ago so even these resources are unable to give me a quote.  

This website is a great starting point to find out what areas are like https://www.areavibes.com/It gives you a total livability score and from there you can narrow down you search. 

@Nkiruka Okeke - That's the case with any website.  

The typical rent collection sites are not what I'm looking for. 

That means that you will need to get those particular ducks in a row before you get rolling.Also, sites like Taskrabbit.com has a lot of folks on there that can help get things put together, setup the spaces etc.

The City of Chicago website should have details on where and how to remit.

Here's a little background on Tenant situation...has 2 or 3 young kids, an adult sister, an aunt with her male friend and the lessee has a male friend, that all appears to live in the apartment but aren't on the lease.

For the most accurate yearly tax figures, you can check directly on the Spartanburg County tax assessor's website.

From googling, it would appear I need to hire a professional.

As inflation drives rent growth, properties in stable markets like the Midwest can continue to deliver returns even in higher-rate environments.Market Conditions Favor Real Estate RecoveryThe commercial real estate (CRE) market has faced significant challenges in recent years, but signs point to a recovery:Bottom of the Market Cycle: CRE appears to have reached its low point in late 2024, with 2025 marking the start of a slow recovery phase.Limited New Supply: High interest rates have curtailed new construction, which should drive rent growth in the coming years.Policy Changes on the Horizon: There is growing discussion about potential policy shifts under the new administration, including a return of 100% bonus depreciation and lower interest rates.