A professional property manager should handle the heavy lifting, ensuring your investment is protected and profitable without adding stress to your plate.

Transparency and professionalism are core to how we operate, and we ensure all properties have clear, insurable titles before closing.

.✅ 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.

Let's cut to the chase:  "A tenant is obligated to follow HOA rules, as they are considered residents of the community and must abide by the same restrictions as homeowners, even though they do not own the property; the landlord is responsible for ensuring their tenants understand and comply with the HOA rules. 

How does the buyer ensure that the proceeds are used to pay the first mortgage?

Framing your position as fair such as explaining the difficulty of finding renters during off-peak months - might help maintain a positive relationship and reduce risks of property damage.Prepare for What’s NextEven if the tenant moves out early, ensure you’re protected.

I do have a fairly high percentage of my net worth (35%) in the PPR fund. 

This ensures a clean transition of ownership and responsibility for insurance purposes.

Also, ensure you're compliant with New York's security deposit laws, which cap deposits at one month's rent.

Just ensure the agreement is clear and formalized.Pooling reserves across properties might make sense if you’re confident in your cash flow and other contingencies.