The problem is that your debt payments are going to basically wipe out that $400K profit unless there is room to increase revenue or reduce expenses.

In the next 4 years my income will drastically increase, but I don’t want to wait 4 years to buy another property that will be an investment.

You know this and the reason I am saying that I am considering in getting a real state license is the connections, the access to listing off market and possibility of earning commission that I can use to increase my portfolio.I think that being an investor agent will help me build a reputation and that can be good or bad.

Or try the reverse - rehab a property in a Class D Neighborhood to Class A standards and see what Class of tenant you'll get.

However, hauling away a truckload of items and cleaning beyond standard expectations could reasonably be charged to the tenant, as it goes beyond normal use.Goodwill Gesture: Since this tenant was great for 5.5 years—paying on time and caring for the property—you might consider waiving part of the cleaning cost as a goodwill gesture.

.✅ 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.

We are asking the current tenants to leave as the property is not in optimal condition we like to have our rentals and we would like to fix it up to increase value and rents.

Harder to cash flow due to 25yr am vs 30yr standard.

They use leverage in some of their funds, which can increase returns, especially if they have a low cost of capital (but potentially increase risk and trigger UBIT issues).

What the investor will have is a long term appreciating asset; that will provide an increasing cash flow as rental rates increase, and steady amortization as the note is paid down.