Building a portfolio allows you to gain experience, develop systems, develop your own approach to managing properties etc.

David, do you know any Hard money lenders that would allow a person to wrap their loan without doing a balloon? 

Form 3115 allows you to restore the fairness in this situation and "catch up" with the remaining $30k of depreciation that you failed to take in the years past.

They don't allow auto payments or automatically add late fees, and tenants would have the option to pull their payment back, which is not ideal.

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

.✅ 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.

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.

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. 

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.

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