My suggestions would be in this order:(a) Determine the type of financing you qualify for - this will short cut the process considerably and save time on investment angles and next steps.

One thing to be careful with though is that if you go the personal loan route, you need to ensure your DTI is still fine and you will still qualify for your VA loan assumption AND the second mortgage.

Renting at FMV ensures the property qualifies as an investment while preserving its long-term utility for your portfolio.This post does not create a CPA-Client relationship.

You don't want them to just be financially qualified but you failed to investigate how they treated their past two apartments. 

If the ARV has risen to $260k and you’re renting it out for $2900/month, you can likely qualify for a higher loan amount.Here are some key points to consider:Loan-to-Value (LTV): A typical DSCR refinance will allow you to borrow up to 75-80% of the property’s ARV, so for a $260k property, you might qualify for a loan of $195k to $208k, which could help pull out most or all of your original investment.Debt Service Coverage Ratio (DSCR): Since you're renting for $2900/month, the loan payment will need to be covered comfortably by that rent.

With some additions, this would qualify for the OMG category, but I think they didn't have that category back then when it was on the market.

This extra road frontage now also qualifies my property to be able to be legally converted into a triplex from a duplex.

I have not thought of using DTI instead of 3x the monthly rental amount in order to qualify an applicants income, but you made a great point regarding the priority that tenants might give a car payment.

Spruce the place up and find a new, qualified renter at market rate.Don't forget to update your lease agreement.

This is where your qualified intermediary takes title to the new property and holds it until you are able to close on your old property.