Have recently started a renovation company with a friend, both of us successful business owners and talented in the trades.

Only "CASH OUT" of your IRA in cash of an emergency or you are at retirement age. 

It was also difficult to assess the heating situation after repairs since tenant refused to provide key to access unit for repairs and/emergencies, citing “privacy and safety” concerns.

.✅ 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.

As a PM, I'm authorized to make emergency repairs without owner permission.

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

My other background for 15 years now is in the trading world.

There is a State of Emergency in effect and anti-price gouging laws apply.

They are simply trading one thing for another.

Then keep $30,000 in reserves in a hysa for emergencies.