I can definitely see how that island looks super weird from the picture I posted. 

Need more info as to what exactly will the $130k will cover that the $86k will not.And the raising the rents *over market value*?

Elise, I am from NJ and my properties are in PA, my PM has never charged that. 1099-MISC is for sub contractor when you pay them, as a PM you are not paying owners because we own the property, we pay you and if anything we should be sending that to the PM, but you should be professional enough to report your income, that income for you is subject to SE tax which you would have to pay. if you are going to charge your customers to cover that cost on top of your normal rate you charge, you may not get any business.

If they are near $200/ month, I expect them to at least cover water, sewer, trash, and basic insurance. 

I am looking for approximately $30,000 to $35,000 to cover all repairs/expenses.

Especially in Florida when every year (almost) they suffer this kind of threats.As a flipper its very hard to find insurance company that will be ready to cover your house.As a home owner for rental: How much will the insurance company will cover in case of total disaster like this?

Can anyone recommend an investor friendly real estate agent that covers the Brantford ON community? 

Around an 8.25 CAP, big value-add property which renovations/parking lot/covered parking etc...In my experience - you need to find an agent or broker to work with who is well connected in that asset class and can bring you deals.

If you get on the websites and see what is listed and take note of the pictures and size and bedrooms and then you watch them eventually you will get a good sense of property values.

@Theodore Arzt Until a perspective applicant has taken the time to fill out an application and you have a clear picture as to their background I would not even waste time thinking about the what ifs.