Reach out to a LOCAL property manager that knows the rental market BEFORE you go under contract! 

You could also explore a jv partnership with a local investor.

Just check the local rules to make sure you’re good to go!

As for offering subject-to financing, this is something that can be advertised under 'seller financing' in our local MLS, and there's investors that search specifically for listings with that marked, so that should introduce your property to a new set of buyers that may not have considered it before.

.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ 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.

It is hard to really keep up with those kinds of trends unless I budget 10k a year in updating the property which I am not going to do.I participate in our local council/mayor meetings.

Here’s the winning formula successful local house buyers and wholesalers use to connect with sellers, close deals, and create win-win solutions:Be Relentless: Show up every day with positivity and persistence.

If you wish to network or ask specific questions about your local market, you can go to your local real estate forum and discuss with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking 5.

Hey Aaron, have you considered a commercial mortgage from a local bank like First National or Bangor Savings Bank? 

I haven't gotten serious yet and don't have a local agent, but I have been window shopping and may reach out.Hi @James Bing, yes I manage my own properties by leveraging technology & local relationships to automate the self managing process.