Determine local/state laws regarding wholesaling and determine if (1) you need to be licensed in the jurisdiction you’re considering and (2) if you’ll be able to operate profitably while remaining legally compliant2.

However, if the property is a long-term hold, the lower interest rate with a prepayment penalty can often result in better overall returns.Another consideration investors should evaluate is how prepayment penalties are structured - whether it's a declining penalty over time or a flat fee - because this can significantly impact their profitability when selling earlier than expected.

Just like any other investment, if you take into account all your costs and buy at the right price, you can still make a decent profit.

He should be digging his heels in every day to make his investor profitable.

Some folks are happy with 5-8% profit margin and others don't look at much under 20%.It is all going to be up to you where you are most comfortable. 

These lease breaks will cost me 100s of man hours trying to fill these vacancies, repairing damage left behind, and pursuing the civil cases.

You'd have to be a builder to really reap any sort of profits from an area as such. 

@Saika MaedaCongrats on pursuing a property with an ADU—it’s a great way to generate rental income!

Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

When you sell the property, and access the equity in the form of liquid cash, you make your profit.