In my opinion, it is definitely worth it to hustle as much as possible to increase that cash flow. 

I would be able to manage this increase but I would not be saving/investing as much money as previously.

What would be your advice on increasing the rents (5yr+ tenants and very under market)? 

Also, many hml's are quite wary of homes that have flooded more than once, and I saw one case recently where they raised the rehab budget and increased their points and interest rate because of it. 

Your appraisal will have to be able to support the increase that amount though. 

I read Rich Dad Poor Dad a year ago and am now looking to increase my streams of revenue.  

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.

This is roughly an hour away from the tanant that shot his landlord last week over a $30 rent increase. 

I own a condo now and do not like how the HOA fees are so high and continues to increase year over year.

The one I ill advisedly bought when I got married for the first time at the tender age of 20, which was remortgaged once and has not increased in value at all since (and the taxes have gone up).