.✅ 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.

The city itself is established, older neighborhoods, better city amenities (museums, arts/music etc), more pro sports, more hills, bigger river, has a streetcar, arguably better nightlife overall.

Its possible in your area that garages and parking are more valuable than units - this is your appreciation. 

My goal is to leverage equity through private money lending (PML) partnerships while building valuable relationships within the local investment community.How I Can Add Value:With 6+ years of experience running various businesses, I can offer high-level and detailed technical insights to help visualize and automate your operations effectively.For example, I’ve developed a dashboard that tracks company expansions across the greater Phoenix area in real time.

* Finally, could you recommend any valuable tools or learning resources?

In that case, you’re living for $2,000 a month—while building equity in the home, benefiting from potential appreciation, and taking advantage of valuable tax write-offs!

It provides valuable market data that offers insights, unlike the free version that offers none.

Their experiences could offer valuable insights and strategies to help you navigate the market.Good luck on your journey! 

And even having a great network is only valuable if you take action with it. 

This would help focus such a call/support for you and hopefully get you more and valuable responses.I would say the blind spots and budgeting is top on my list.