The issue I see most is the cashflow gets crushed by HOA fees and the added headaches of having them tweaking rules etc. 

That might include things like adding units, converting commercial space to residential, or finding ways to boost income (like adding parking).The key is recognizing opportunities while walking the property, and that takes experience.

Which makes my answer, as opposed to yours, applicable.Especially since I qualified mine by adding "...unless she adds more real estate work"Your argument reminds my of an old joke:- Doctor, will I be able to play violin after this surgery?

I saw their ads on BP. 

Also, the original septic is built for a 2-bedroom/1 bath home, but now the sellers have added another 3 beds and 3 baths.

In my case, flood insurance was under $1800/yr and for the numbers made complete sense for me as a good deal with that added cost.4) Flood zone AE does not directly impact resale value, but can reduce the number of buyers considering your property which can lead to slower sale through time and potentially lower prices.  

You are local and adding value add!

Roger that @Brandon Vukelich, but I don't see lenders adding STR revenue to the actual property valuation in the future.

I would consider adding loss of rents coverage.

As an example, my neighbor added a second story to her home and the contractor gave her an estimate that she agreed to.