By managing yourself, you keep that money in your pocket.✅ 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.

If you keep the property in your name, but allow her to live in the property, I wouldn't charge her any rent. 

For bookkeeping purposes, I recommend designating a separate bank account exclusive to the house hack activities to keep some sanity.

If an in-person visit is not feasible, we can easily arrange video tours to accommodate your schedule.

Also, long term, I expect Sac will enact tougher restrictions on STR, given the intense housing crunch we're experience, so I personally don't expect that to a be a good long term strategy.

We do not have a resident benefit package, and we keep our tenant fees very low.

It has to be a personality trait.

Keep your payment at no more than 35% of your income and minimize your credit card and auto debt.  

And what if the one person you didn't check has a criminal background, has collections, and more?

While an LLC can offer liability protection and tax benefits, it’s not essential for a single property—personal liability insurance and an umbrella policy may suffice for now.