2024 will go down as, "The Year of Taking Action".Getting back in the game came with some challenges.

The email was short and challenged us by implying we were looking for investing planning and not tax planning.

I've had some investments perform better than others but section 8 rentals were the one that were most challenging to sustainably operate and my worst performers over an extended period of time.

The biggest challenge is time to manage a property.

Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

@Jay Hinrichs @Jonathan Greene @Nicholas L.you have all helped me to really consider what type of challenge / path I want to get into, and all this information is excellent.

We appreciate your support and understanding during this challenging time.A medical note attached simply says "1 year leave from school for medical reasons"Please advise on what is the best recourse in handling a situation like this?

I wasted too much time trying to piece it all together and when you're in different states it's all the more challenging to make sure everything is legit.

In my experience, finding cash-flowing deals on-market can be challenging here (1% rule can be hard to find) but not impossible.

Then progress to permits and then building.You could also just do it and hope the city doesn't notice, which they probably won't.Your challenge will be getting Certificates of Compliance on the units!