The sides were joined, roof seam reshingled, exterior wall join had a strip of siding place on it. 

Prices have gone through the roof in Ludlow in the last year to the point where most of my analysis only breaks even if I am being conservative.

Ideally you would find a company that has everything under one roof.

My property is currently my primary residence. 4) Can I even register the property as a rental property when it has some serious code violation issues that might affect the safety of residential use: such as electrical issues, roof restoration, etc.? 

(I do not live in Orlando, my retired father does)... and my father takes care of all the maintenance (repairs, hiring contractors for electrical, HVAC, roofing, etc.) as well as showing the property for leases, he is my hands and eyes there... all for free, I do not pay him a salary or any compensation, and he does not want one. 

@Austin JamesUnderstand the area, the current tenant base,the median income, is it in a flood zone, the age of the asset, the condition of the plumbing, the electrical wiring, the fuseboxes, the age of the roofs, the age of the mechanicals, the condition of the foundation, the drainage of the property, does the property have a C of O, is there ny environmental concerns such as oil tanks being buried, the current property management company, what are the amenities.These are just a few things to look out for.

My plan is to have a nest egg of money for each property in case things go wrong- long period of vacancy, roof/water heater/furnace replacement.

One thing that may help is replacing the roof - a lot of companies either wont write or overprice premiums for homes with roofs over about 5-8 years old because it's a replacement waiting to happen with the next hurricane.

Roof is 12 years old, he was looking to refinish the parking lot but just got a quote and it was for 7k more than he did last time so not sure if he is going to to that now.

How much is a roof?