I like the cash flow on them, if you rehab them right the first time it won't be a money pit. 

Some people are able to save money and budget and others are not really good at it.

I start by telling them we have a lot of money tied up in the property, and we've been burned by folks that wanted us to believe the best of them.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

Quote from @Enrique Toledo: I came across a really good seller financing deal and I would like to purchase it as my first deal but I don’t have enough money for the down payment.can I use a lender of some sort to give me money for the down payment?

It was an easy way to scale up with no money out of pocket.

That helps you recover some of the money so if things proceed to a lockout, you're not as bad off financially.

Does it make money?

You are bleeding money now, but each year it might actually get worse depending on the financials. 

By managing yourself, you keep that money in your pocket.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ 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.