Couple is divorcing, husband wants to keep the property; wants ex-wife's name off of property/loan. 

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.

There are still a lot of opportunities for BRRRRs so I'd encourage you to keep your eyes open.

Also keep in mind when I started funding investment rentals in 2002 for CA investors 100.00 a month cash flow was the goal and accepted.. and even break even or a little negative was fully acceptable in markets with historic appreciation..

Surround yourself with a support system and keep pushing forward.4.

Masthope had been rumored to be limiting STR, but it seems they are keeping their eye on the fallout after the big court win in Lake Ariel - https://www.timoneyknox.com/reversed-short-term-rental-regul...

keep in mind 2.9 % or really any mortgage in the 4's was a once in a investors lifetime situation.

Keep what you already have.

I just want it to work and be a positive experience because I know that will keep me motivating to continue investing and building my portfolio.

Working in a busy property management company, I'm often asked for advice on camera and alarm systems, and in rougher neighborhoods sometimes it can be a toss-up on whether to keep a property boarded-up between showings.