Hey BP,I know this question has been asked often, but I've been struggling trying to find an investor-friendly insurance company.

On insurance side of things, there is a lot of variables.

It isn't having paid off properties that offers security, there are still taxes, insurance, maintenance and management involved. 

Living in one unit and renting out the others allows you to deduct 75% of expenses like mortgage interest, property taxes, insurance, and shared repairs as rental expenses, while the remaining 25% applies to personal use.

Tampa can work, but yes, taxes and insurance are higher and might keep cash flow tight.

We were initially looking out of state for a potential move and or investment property just because the property taxes without being able to homestead, plus high cost of insurance, and harsh weather on homes made me feel like it might not be worth it.

There will be no assessment for increase in taxes or insurance so remains at $1935.

Explore the possibility of doing liability insurance instead, if you don't have much equity it may be your best, and much cheaper option.  

My payment with insurance & taxes is $1425 a month.

Enough immediate cashflow to balance out the mortgage, taxes and insurance.