I'm ready to start looking at properties and identifying a contractor/s I can work with, what type of insurance will I need to make sure my business is properly covered and does that have to be renewed/added to each house I flip or is there some sort of umbrella policy that I can add and remove properties as my business progresses?

Depending on the carrier this can be exclusive to Category 1 and above Hurricanes or it can also include Topical Storms and/or Tropical DepressionsTropical Cyclone - A little broader in that it will generally include any storms that originate from the Gulf of Mexico regardless of the status (hurricane, tropical storm, etc.)Wind and Hail - The broadest in that it not only covers any storms originating from the Gulf of Mexico but any wind and/or hail damage regardless of where it originated fromThe reason why you need to pay attention to this particular deductible is because it will be percentage based deductible; keep in mind that this means that if your cost of insurance on the dwelling increases, so does the deductible.

I would contend that if, as you say, the rent barely covers the mortgage, you will end up losing a lot more than that over time by holding onto the house.Repairs and maintenance on a house are not cheap, especially on one that is 100 years old.

I've nothing to add, you covered it. 

Your rental income doesn't cover the value of your equity let alone any expenses.

We added on site laundry and redid all the landscaping.Doing all this allowed us to increase rents 30%+, which means the three rented units cover the PITI for the property so we have no housing costs.

From the rent I have covered property tax so in 2018 I will not have propblem paying property tax and that is why I went to the county and got offer for installment plan for 5 years start this June which again I can afford it. 

I have a friend who purchased an empty lot a few years ago, developed plans for around 200 apartments to be built, but didn't have the resources to cover the construction/interest costs until revenue could be generated. 

I don't have a lot of emergency funds to cover of it.  

You still might get stuck with the overage but you can cover some of the costs this way.