If long-term rentals don’t cash flow, short-term or mid-term rentals (Airbnb, traveling nurses, corporate stays) might work better.

Start with BiggerPockets Ultimate Beginners Guide (free).

He likely needs to stay where he is, save up money for a downpayment on his own, and buy when HE is ready.He's not ready. 

I am sorry that the storm that passed through just prior to your stay required emergency roof repairs. 

.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

I generally stay out of politics, but I’m interested in hearing investors' perspectives.

Hey Marc - Offering free Netflix can be a nice bonus for guests and make your property more appealing, especially for longer stays.

Understand the multi-family market, scale up portfolio efficiently, focus on value-add opportunities, build a reliable team, stay informed, and engage with the community for support.Good luck!

You need to learn how to analyze property and determine if they are a good investment.Here's a guide that describes how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...

I could go on for days about these people but stay away from them like the plague.