Have you taken the time to search AirBNB and VRBO in those specific areas to see how many STRs are operating?

If you have an adjustable rate mortgage and it is likely to increase significantly in the future, rent growth rate may not compensate for this and cash flow is likely to get worse over time.

.✅ 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.

Some great information here - thanks for taking the time!

How many times can you spend $1500 to get an 88% return?

Too many investors waste time chasing bad deals, overpaying, or relying on outdated strategies. 

We have emails, video conferences, secure portals etc etc.We do have a physical office, and half of our clients are local.

The definition of poor initial cash flow has changed with time.  

Any guidance would be most appreciated, so we can be better prepared for our tax returns next year.Thanks so much for your time !

The last time I looked, a $1 million policy was about $200 a year.