If you are looking to just do some cosmetic upgrades, you are going to search out a property with good "bones" and mechanicals that do not require major CAPEX items...like roofs.

However, the description states that new siding, new roof, and windows have been updated.

Anyone know of what insurance companies will cover a 1950’s home with a low pitch roof?

You will wright them off but as a capital expense over the years like a roof/house purchase etc. once you post the house for rent then anything after that like utilities and basic repairs will be a monthly or same year wright off. 

New roof on home and garage, electric update, kitchen, baths, floors, front porch, landscape What made you interested in investing in this type of deal?

In any case my tone is not conveyed well through writing this, I’m not advocating that this is a good practice.

It is all coming from our "through the roof" property taxes.Yeesh- forget the respect, I've lived without it.

The same amount should be set aside for capital expenditures (roof, paint, carpet) and you have nothing for that. 

Now I would like to replace the whole roof of the house.

If you want to change the size, rise/run, location, etc. you're going to need permits, etc.If you hire out a total rebuild, the contractor will most likely have to be licensed and insured.Honestly, I'd do this myself.