Quote from @Frank Pyle: Obstacle is getting a 1007 with realistic long term rents. 

While you are willing to work with them, they are apparently happy to live rent free and don't seem to care about you.I had a long term tenant (5 years) who stopped paying the rent.

20% is about average for a short term rental as far as management fees go.

Knowingly buying into the red just because of financing terms is a very unhealthy way to invest.

Tax deductions / write-offs should be a second concern.There are some rules that you need to follow to treat a short-term rental as 'active'(non passive) income which would allow you to offset it against other forms of income such as rental income / wages.

Focus on long-term guests, like corporate clients staying 30+ days, because it’s easier and brings steady income.

@Jordan Meltzer congrats on the mid term biz and your success. 

These penalties can vary depending on the loan structure and the lender's terms.

Really depends on what they are looking for as well as long term plans.

Some lenders offer creative solutions, like a cross-collateralized loan, where they use your existing equity as security without refinancing the duplex.Another idea is partnering with private lenders or exploring a second-position mortgage, depending on your lender's terms.