Anyone have some first hand experience with RADD/REIT that Dutch Mendenhall runs.

If I pay it off, I could maximize cash flow earlier, reducing financial stress and allowing me to focus on other ventures or simply enjoy life more.On the other hand, I know some people advocate for keeping cheap debt and using the extra cash to invest elsewhere for potentially higher returns.Why I’m leaning toward paying it off:Security: No debt = peace of mind.Financial freedom earlier: A fully paid-off rental would give me a significant monthly cash flow?

But you can't do that without investors assuming your average guy/gal and I don't think I'm cutout for that and that is a lot more hands on. 

In the last few years, they've made illegal:-Rent controls of any kind-Limiting of fees or screening charges-The ability of HOAs to regulate STRs or LTRs in their neighborhoodThat's just the start.

When a lawsuit is started, there is something called the complaint.

We started with an offer of $1,000, but after some back-and-forth, we reached an agreement at $1,500.

.✅ 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.

Right now the only utility at the garage is power so basically I am starting with a frame and a roof. 

It sounds like you are off to a great start already especially by educating yourself! 

I started with two remodeling projects and have since completed three new construction projects.