I invest out of state because at the time, I could not find anything that would meaningfully cashflow, plus a $150k deal was a LOT less scary than a $800k deal!

It’s their full time livelihood to make transactions happen.  

Thank you for your time and patience!

No one recommended a bank at the time for the SDIRA, it was only trust companies as the custodian.

I'm having a very hard time with them and on the verge of losing my earnest money on a house purchased to flip.

Easy Street is a good option BUT you need CASH in liquid checking/savings for down payment of 20% and BIG chunk 2-3 times loan amount to buy out of a prepayment penalty.

At the same time you're figuring that all out, get your brother and friend under a lease, or at least, a written agreement both parties can agree on.

.✅ 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.

From what I've seen in this area right now, it seems like you'd have a hard time paying market LTR rents and making a good spread. 

And i've only done it three times.