You could give them a thousand bad reviews, if they are the only person in town offering a specific type of product, people will still do business with them.

It’s important to recognize that your landlord likely isn’t thinking about selling the property right now, especially given their personal circumstances.

Personally, I advocate for a long-term investment strategy and would recommend investing the funds, provided you are comfortable with the expected return on investment over time.

It depends on where you want to live, income, personality, and other factors.You could buy a large home and rent out the individual rooms to cover expenses, but this comes with problems.

Quote from @Jessie Dillon: just my 2 cents.. i'm not a fan of the syndication model. there are better ways to invest more passively where you have more of a say in what goes on, can achieve higher returns, and can have your personal interests at a higher priority. 

.✅ 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'm not a professional Tax person.

Figure out which best fits you and your personality and take it from there.  

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc.