I’d suggest focusing on securing solid DSCR loans—like those from thelender.com, which lends up to 80% LTV, considers STR income, and operates as a direct lender.

Understand what you are investing in....is it a secured loan, unsecured loan, membership interest in an entity that deploys capital like a feeder fund or direct membership interest in an entity that is the deed holder? 

I would do a direct mailer in my area and try to pick up another owner occupied.  

I think one thing that is helpful, is to be more directed in your question and what you're looking for with regard to coaching.

DM me, and I’ll point you in the right direction!

@Levi Perl Since your single-member LLC (SMLLC) is a disregarded entity, all rental income or losses are reported directly on your personal tax return rather than at the LLC level.

But, you need to talk directly to the person whose name is on title. 

As a few have mentioned, the best way would be to call the listing agents directly, but depending on how much time you want to dedicate, setting and going on multiple appointments with different people could prove to be time-consuming. 

.✅ 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.

Start with Reonomy or Costar to identify all the 100+ units in your target market (on and off market) and then see if you can get into direct contact with some owners.