You could have picked it up, flipped it right back on the market for $300K without lifting a finger, or done a basic builder-grade renovation and sold it for $625K+.Also, most homes in the South End fall under RMF or R6 multifamily zoning.

Are we possibly cutting ourselves short here with a deal of this nature?

You can manage remotely although you need someone that can reset units and pick up any trash. 

This increases risk because every time a new person is introduced to the equation (allowed at the property), they bring with it just a natural amount of risk. 

(If then, your occupancy should be up naturally compared to 3 months ago without doing anything) If you want to compare occupancy, you need to do year-to-year comparison.

The current property is propane-only, and while natural gas is available, the cost to bring the line is around $40K–$50K.

Are we possibly cutting ourselves short here with a deal of this nature?

Doubtful, given the  serious nature of the maintenance items. 

Natural disasters and requirements for 100% hurricane coverage have had a dramatic impact on HOA's insurance costs, and also affect Buyers due to lending requirements. 

It's just that I see how far off we are and, being inexperienced, am naturally inclined to think I'm being too cautious.