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House hacking a duplex, even with negative cash flow upfront, is a great way to build equity while learning hands-on.

This deal proved to be the perfect balance of financial gain and personal enjoyment.

More importantly, I often learn something!   

Well, STR can work well for people who own a vacation house for personal use, and just want to generate some extra income when not in use.  

So I've embraced an attitude of continuous learning and adaptation.

But since you are new and learning, don't decide on what it has to be.

.✅ 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.

So when you build your pocket neighborhood, which is an interesting concept, what's to stop an undesirable person from moving in.

As a disabled person, I want to be in real estate, but I know I am limited.