I wouldn't worry about the $1000 payment.

I think there's a path to refinance that would flip me into positive cash flow, but I'm coming up short on ideas. 

In this type of situation, they want low interest rate with low down payment also.

@Jordyn Ohs Assuming your heloc is re-advanceable and the rate is higher than your mortgage, I would suggest you pay your HELOC down as quickly as possible with any cash flow from the properties.

The low down payment house hack is the way to go.

Purchase price: $900,000 Cash invested: $15,000 6BB/3.5Bath 4000sf on 3.4 acres near several wedding venues.

I have some brand new homes in Phoenix that cash flow with 25% down.

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.

The only other option would be to get a coborrower to bring the down payment or get seller financing with a lower down payment. 

A cash out refi should take 2-3 weeks with most lenders, and you should have only an appraisal a credit report fee as upfront costs.