.✅ 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.

i'm local and can connect when your time allows.

The primary thing you're going to run into is whether or not a lender, at purchase of the property, will allow there to be a secondary lien on the property.

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.

I know federally backed loans are required to give 30 days notice but I believe that because it is a triplex and the other two units aren't owner occupied it allows me to do a 3 day notice. 

Finding a condo that allows Airbnb/STR will be challenging, they're rare and cost more because of it. 

The loan will be used to payoff the 49% partner and allow me to take some cash out.

Quote from @Alex Moazeni: You are making the common mistake of allowing a tenant to push you around.This is your property.

The CA Dept of Insurance allowed a 34% increase in 2024. 

It also identifies signer names within the documents, allowing you to uncover the owners behind the ownership entities.Currently, lenders primarily utilize the platform to monitor client and bank activity, but we're exploring options to tailor the tools for investors.