Just do thorough research on the local market and have a solid plan for managing the properties remotely.Good luck!

You might consider: Consulting a Real Estate Attorney – Your emails may possibly prove misrepresentation.Requesting Public Records – A FOIA request might reveal why the city denied you but later approved the duplex.Escalating to City Officials – Bringing this to local officials could expose inconsistencies.Exploring Tax Write-Offs – A CPA might help offset your financial loss, if it is possible.I’d definitely seek legal advice.

.✅ 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.

Local credit union.

Geographically locally where is your house in the landscaping?  

My local REI buddy called today.  

I’m a local realtor and can help you out as much as possible  

Wrapping 3 properties into one blanket loan shouldn't be a problem, save these are sitting on any sizeable acreage.You might get lucky and find a unicorn local bank or credit union that would consider that kind of leverage, but I would say overall, those terms are very unrealistic.Cheers!

As I dive into all the different paths I can take (single family vs multi-family, short term vs long term, cash flow vs appreciation, local vs out of state, etc..) my mind is scrambling and I've ended up doing nothing at all.I'm looking to join a mastermind that meets consistently and can really motivate one another to take our businesses to the next level. 

BTW: most owners that have hired a PMC, don't want to speak with you, much less meet with you in person to hear a hyped-up sales pitch.Also, you want to do rental arbitrage - so, you will need to be properly licensed to manage properties you do not own as required by your state & local laws.- why would an owner want to do business with someone NOT properly licensed?