.✅ 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.

I can't help on the mastermind front, but I did grow up in Central IL and can relate to the "something goes wrong with a property, now I'm spiraling, and this was all a terrible idea" feeling.

You also will need to have multiple lender relationships as you grow. 

As we grow we want to make sure we have the infrastructure to keep growing.

Similarly, 73170 is in a growing area with good schools and strong community appeal, making it attractive for both renters and families looking to buy.

I’ve got a few rental properties under my belt and am now diving into value-add multifamily projects to grow my portfolio.My focus is simple: build wealth, create opportunities, and enjoy the process along the way.

Posts like this are part of my journey to learn, network & connect with experienced professionals like yourself who have valuable insights to share.I also want to apologize for the late response—it’s been a busy few days, but I didn’t want to miss the chance to thank you for your input.Looking forward to learning & growing in this space & who knows, maybe one day I’ll be offering you in on an investment idea or I'll be the one offering advice to new investors!

For us approaching retirement age, we want to have a mix of mortgaged properties and properties with full equity to leverage instead of relying on saving up for the next investment. 

Let's just say even seasoned syndicators are having a lot of trouble raising capital these days.Personally, I would focus on growing as a pilot and getting into mainline (if you aren't already there) and into the captain chair as quickly as possible. 

There’s a ton of investment pouring in, job growth, and a growing demand for housing.