I likely purchased this property too quickly as it was the 4th property we toured and we didn't negotiate on asking price as the house was previously under contract and my agent advised against lowering.

Quote from @Rick Ilich: Thank you very much for the quick response!

.✅ 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.

Sold it for a profit fairly quickly.

What pitfalls or challenges should I be aware of when scaling up quickly?

Quick turn over time.

I did a quick search and there are 187 total rental listings in Marion Oaks in the last 90 days. 90 are vacant listings, 18 canceled, 70 that have leased, and 4 pending. 

When we spoke, I alerted you to the need to make the quick repairs, and you agreed to allow access to the space to get things back to top shape.

If I keep doing the same strategy, putting more money down upfront, I will generate more cashflow now but am delaying how quickly I can purchase houses. 

A quick call with a local attorney can set the record straight and help you navigate this without drama.