Purchase price: $220,000 Cash invested: $30,000Currently house hacking.

Given these numbers and his research, he believes it may either cash flow slightly or at least break even, which has made it a bit more difficult to find an end buyer. 

Purchase price: $160,000 Cash invested: $35,000 Purchased this property as a turnkey investment at the 1% rule moving equity from another deal.

Between the equity on the condo and the extra cash you have, you can purchase 2-3 homes. 

Despite wanting to handle it a few other ways I reached a small cash settlement with him to drop it.

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.

In my home market of Florida, our insurance rates have made it much harder to have positive cash flow on a CRE deal.

I plan on getting a property every year until I retire if I can find a good deal that cash flows positively.I have a very close friend whose stationed in Columbus GA whose a real estate investor and owns rentals there!

Additionally, based on your numbers, it should definitely cash flow. 

In this later scenario, you need all cash, just the same as if you were doing this old school style at the courthouse steps.