One of them has a clear path to return a profit and is executing that plan well. 

@Krystal Stone I would be sure to check and see how many clients (youth) they are planning to house at one time.

@Eric Gerakos In theory that's the plan.

Is it tied to changes in the market, a response to new regulations, or part of a long-term plan?

@Ramsey Doumani This is a great plan.

But what is really important is that you understand the terms of the loan, including the length of time and when you can expect to get the money back, how it is secured, and the process of getting it back if things don't go as planned with the investment.

There's other items such as this where it may be helpful to talk to a CPA/EA for a little tax planning, especially since you'll likely get caught up in the passive activity loss limitations if taking bonus on a single rental property as I often see.It's also useful to mention that even if you do the cost seg study (I'm assuming you're doing one to be talking about this), you'll still benefit from accelerated depreciation in the form of shorter useful lives on the assets where you received bonus from.

.✅ 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.

I read about a 1091 exchange and if i reinvest my money into another property within 6 months then ill avoid paying the taxes on it. is this a good plan, if not do you have any other suggestions.  

Excited to hear about your plans for 2025—let me know if you ever want to chat about the market or need any help finding deals!