Any amount over your adjusted basis in the property (initial cost minus depreciation) could be subject to capital gains tax unless you reinvest it strategically.2. 1033 Exchange (Involuntary Conversion): A 1033 exchange (involuntary conversion) is specifically designed for situations like fire, natural disasters, or eminent domain.

I’ve owned this property for four years, and this is the first complaint of this nature I’ve encountered, so I’m curious if, by leaving it as is, I could go extended periods without facing clog issues.Any advice is much appreciated!

We are seriously considering  rent to retirement properties given the relative passive nature.

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

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.