As you collect rent throughout the year and or years you will be increasing your capital/reserves.

The property was brought back to better than original luxury status, therefore increasing my rental prices from $950 to $1200 per month.

It will come at a cost of fees and some time though.Now umbrella insurance and liability insurance on the property is definitely an obtain and increasing the policy increases your protection but one thing that is always unknown is how much a claim will be. 

We purchased the property with a conventional loan and 5% down, 30 year, and a PMI obviously.We are doing some significant updates and upgrades that will increase property value.

We are undecided on whether to put down asphalt or gravel to help increase value to our home & property.  

Lincolnville is way over priced now that the hipsters have discovered it and of course it was flooded during hurricane Matthew...now the city might make you bring the buildings up to code which can include lifting the houses up ....I would be very careful about any "deals" that suddenly pop up ...here is an article that explains ithttp://staugustine.com/news-local-news/2016-10-28/hurricane-repairs-st-augustine-flood-elevation-standards-could-be-concern

@Alexis Guini You're an agent, I assume you're familiar with standard inspection and financing contingency clauses?

I purchase properties in Michigan and supply investors with those properties once they are performing to our standard.

But they also COULD show that the ratio starts decreasing (or increasing) with larger square footage.

Are you sending first class or standard mail?