Could be.I think that for most individual American investors leverage is a critical tool. 

•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.

One thing to note when getting conventional mortgages and spouses.There is a 10 limit per person for conventional financing.You can either do 10 conventional in each person's name which would be 20 mortgages for 2 people or if you do the mortgages jointly, will only allow 10 in total.My thoughts are not to own joint assets until you are both married. 

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Quote from @Anil Shah: Since I read a townhome, I assume there is HOA - do they allow STRs?

The primary thing you're going to run into is whether or not a lender, at purchase of the property, will allow there to be a secondary lien on the property.

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.

Oh, and given the longer parcel length, does the city allow ADUs? 

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

If you're a relatively new multifamily operator, you'll likely be required to hire a professional management company (inexperienced owners are typically not allowed to self manage the assets).