@Jamie Parker pay for some one-on-one time with @Jonathan Greene - it'll be worth it!

There are certain things that require experience that DIYers just can't get right or spend way too much time trying to do.

This happens all the time, usually with heirs, but it can be squatters as well.

They also change based on time of year, and availability of contractors. 

Does anyone have suggestions for retroactively estimating your time? 

The rest just falls in place over time. 

Be very careful with this as a first time project! 

.✅ 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.

There are not a lot of comps and sales as of now but more are being built so time will tell with your ROE.

I've been there a few times, but know nothing of the market there.