Put yourself in their shoes. 

So I suggest getting a ‘best guess’ figure based on several sources (Airdna, Rabbu, STR Insights - don’t rely on just one) and then build in some conservatism and see if you are still comfortable what your pro forma kicks out.

So I would definitely say getting into a property if you can comfortably do so is the best option.

Get out of your comfort zone.

Get out of your comfort zone.

But you may be more comfortable with earthquakes, or tornados than hurricanes. 

Make yourself comfortable with both the contractor's ability and with their price.

After renting out the finished basement and one of the main units, we'd be paying a very comfortable amount for our part of the mortgage, and upon moveout we'd be breaking even with PITI + maintenance, capex, vacancy which is what we wanted to achieve.

Cool , good though to brain storm here as you get fabulous advice.. but next time see if you can JV locally and then will feel more comfortable

Get out of your comfort zone.