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. 

If you didn't have boots on the ground, it would be tough, because you'd end up with some cash leaks.  

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?

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.

All of a sudden Bldg Insp said we HAD to have 2 stair cases down plus an egress window to the lower flat roof & then install a fire sprinkler system.