I would like to keep the property and turn it into a investment property but it does not look like it will cashflow positive once turned into a rental.

I believe HA still has the option to wait 24 hours before approving them.As a Premier Partner you have access to phone numbers during the inquiry phase.I have seen where others have provided feedback form other booking sites and I have not seen any positive feedback on them.I am even getting bookings through Expedia now since they own HA.

@Jabari Jones,The HELOC will not impact your DTI until you draw from it.

Have you had any positive, or negative, experiences with seller financing deals in the past?

The tax impact is generally significantly smaller than the benefits of leverage and the resulting higher cash-on-cash return the IRA receives, but does introduce the filing complexity.The repayment terms would be those offered by the lender, not anything specific to the IRS rules. 

You are probably looking at about $150 positive cash flow per month long term.

You may want to reconsider your ultra conservative investment approach in order to grow and actually achieve positive cash flow.If you are buying homes worth 50K or less and renting for $850 + per month you are not doing as badly however you should try to find a way to pull all your dead equity especially before the markets turn and you end up losing it all.Paying off rental properties is not investing it is hoarding of cash and is extreamly expensive.Just food for thought

If the contractor is paying for building permits, check to see if that includes impact fees, utility meters, etc. 

They should know them, down to a decimal point, and be able to explain how they were determined and how those figures impact your bottom line.

Should bring in $300-$400/month positive cash flow.