I am looking to begin the process of a 10+ year plan to build out a sustainable REI enterprise which would ultimately provide me with significant passive income and net worth to make a legacy business for my family.

Unless you have a solid plan to turn this around, selling now and cutting your losses might be the best move.

.✅ 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.

You’d need a clear exit plan and enforceable lease terms to protect your investment.Think about the following:Tenant Risk – Can they truly recover financially, or will you face another eviction situation?

Would you rather set it and forget it and not need to refi again or rather take advantage of low/no closing costs on this loan and plan to be more aggressive on your rate at the time of your refi?

You need to make a written plan with him to get this over the finish line, with cost estimates.

I'm planning on doing a str loophole so low priced str won't work well for me 

With the exception of building a trailer on the property (these are hard to finance), this sounds like a good plan AND if you are using it for your business AND your business pays more than 50% of the rent (if you have more than 1 tenant), then this is a more financeable property in the eyes of banks and credit unions as it would be consider a commercial "owner-occupied" property. 

I am currently 36 years old and planning to start my real estate investing journey this year.

They were thinking of planning another one that required massive loans (7 figures).