With out that, there is no proof that it will perform.Do you have a full estimate and plan for 3 years on the property?

.✅ 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.

Any advice would be appreciated.I would first talk to a real estate attorney or a foreclosure attorney to make sure that the way you plan to do things passes muster.

@Ramsey Doumani This is a great plan.

If you don’t care about maximizing loan amount then you could start whenever.

He's a CPA with a focus on strategic tax planning.

When the second phase was built, the units have the same floor plan, but they added individual heat pumps and individual hor water heaters in each unit, so that they were on the occupant's electric bill. 

The open floor plan and natural lighting make the space seam bright and airy while the community features like the tennis courts Pool and guard service will make you feel at home.

However, if the 401k has business income, it will be subject to UBIT.An IRA is not subject to capital gain taxes because it is a tax-deferred retirement plan.

You could also take out equity if you want to keep the condo and use that for another investment, but I’d be careful about over-leveraging.