As a newbie, I’d love to connect with local investors and agents to learn more about the area and refine my plan.

There will be before pictures, after pictures, and a copy of the invoice from the vendor.

HOA management for a bunch of peripherally involved out-of-town investors is probably a great opportunity pass along overpriced contracts to your local buddies. 

Talk to local investors, study rent comps, and understand how leasing cycles work in your chosen market.

However, especially if the investor is buying in an area they are not familiar with, they probably will not know the nuances of the local area. 

These software's can run all kinds of reports and also help you with rent collection and accounting for vendors etc.

.✅ 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 will DM you a link to our preferred insurance vendor for a quote. 

All you need are local vendors you know...with texting and internet, and good tenants.  

To help avoid a lot of these issues I would think about buying a "Modular" or use a "Tiny Home" vendor who offer these in many states.