I sense a bit of "purpose" that is driving you that you may not have thought of.

If there is anything I could do (drive by, analysis/insight on the area) I would be glad to help.

In terms of the areas, you will be best served driving it.

In suburban Chicago, historical significance or celebrity ties might create a niche appeal, but they won’t necessarily drive up the home’s market value in the same way as location, condition, and local comps.For a short-term rental, though, it could be a great marketing angle—especially if the person is well-known and has a strong local connection.

I’ve isolated these three markets as they’re all within driving distance from my home and seem to fit my budget of $100K-$200K for purchase price.

Its also a good idea to keep any receipts (I use a google drive folder, they have a scan function that makes uploading receipts a breeze)

Use tools like:Airbnb Analytics: Monitor impressions, clicks, and overall CTR.IntelliHost: Analyze your listing for category placement and CTR improvements.RankBreeze: Track your listing's performance and ranking changes.You can also A/B test your photos by rotating lead images or running Meta Ads (Facebook/Instagram) or Google Ads to measure which photo drives the most engagement.The Airbnb algorithm is continuously evolving and every host should pay attention as new features are rolled out. 

Their clear incentive is to bet on falling interest rates between now and debt maturity.A small handful of owners are forced to sell due to a looming balloon payment that a refi won't cover, but you're not going to find one of those by driving the market when any commercial broker can just look up properties on that basis and start making calls. 

Just drive by to see.

At 19, your friends may not understand your drive.