Not questioning your judgement/assessment, just trying to understand the situation to best advise you. 

Key Factors for a Good Seller-Financed DealCash Flow: Rental income should exceed monthly payments (PITI) by at least 1.25–1.5x.Purchase Price: Compare to ARV and market value for fair pricing and equity potential.Interest Rate: Aim for competitive rates; higher rates must still allow positive cash flow.Amortization/Balloon Terms: Favor longer amortization and align balloon payments with your exit strategy.Down Payment: Lower upfront costs reduce risk but should meet the seller's expectations.Flexibility: Seek no prepayment penalties and fair late-payment clauses.Property Condition: Ensure the property’s condition matches terms through inspections.Seller Motivation: Assess the seller’s willingness to negotiate favorable terms.Exit Strategy: Have a clear plan for refinancing or payoff at term end.Portfolio Fit: Ensure the deal aligns with your financial goals and risk tolerance.Vetting multiple deals and consulting professionals is crucial to making sound decisions.

Given that I would pay 3/4 of the property's assessed value I think this could be a great opportunity.

Owners were charged an assessment (several thousand dollars) in 2023 to put into reserves, as per the new rules after the Surfside collapse.

It would be a good idea to assess your tolerance to risk and then plan something like that, but using a heloc is going to be around 9-11% in this market so to pay something off with lower interest rate to borrow more might not make much sense.

I believe it is completely reasonable to have a clause in your lease that places a cap on utilities with any overage (proven by a bill) being the responsibility of the resident.Our clause states that any electrical bill (we don't have gas, and water has never been a problem) that is over double the same month's bill from last year will have the overage assigned as a fee.It is important to keep your bookkeeping straight if you do assess a fee.

That showing was yesterday  Would love if you give feedback on actual listing.

Happy to help with listing if that’s the way you decide to go too! 

Only with a definitive goal can you accurately assess your options.What I hear you saying is that you do want to build a rental portfolio. 

If you're targeting Section 8 tenants in Chicago, I'd suggest listing at the fair market rent of $2000.