Well, there is a law in certain areas on how many roof layers you can have. We have one asphalt layer however we do have other layers (not asphalt). Legally we can not have more than two asphalt roof layers on our house. So, even if we had two layers of asphalt we could add the steel roof over them. (you just can't add another asphalt layer) We made the decision to keep the asphalt roof because it would be thousands more dollars to rip off the old roof and dispose of it and we are not required to rip off the old roof. Ripping off the old roof, according to our research, would not benefit us or extend the life of the new roof. Many people around here have metal roofing now and luckily I have seen them being installed. Every one I have seen installed has been installed over the original asphalt roofing. Most likely people did this as a cost saver. This is one of the benefits of metal roofing. The cost of the metal roof is nearly the cost of a complete tear-off plus the new installation of an asphalt roof. if we had to do a complete tear-off we would not be able to afford a metal roof. There are two types of metal roofing. Ones that can be installed directly on the roof deck and those that are meant to be spaced between the roof deck w/ purlins. These roof are more rigid and usually cost more. We wanted the metal roof to be installed over purlins because this leaves an air gap = more insulation for our house. If you need repairs to the roof deck you would have to remove the shingles in that area of the house. Maybe that is why your husband is in favor of the tear-off?? So, we came to the decision to not do the tear-off because: -it was more affordable -not required -did not harm the house or new roof -renee

From the photo, it appears that the roofing material is a low end composition. The folded over piece is evidence that the seal tabs didn't and the wind got under it. The deteriorated condition of the shingles usually doesn't occur for fifteen years or so. Should the roofer not satisfy you contact the mfg.

You will get more responses if you post a picture.

What a darling house! I'd play around with the color blocking and not assume the siding and garage door have to match. Maybe paint the garage door to match the brick, as in @celerygirl mock-up, and then decide what to do with the siding. A new front door and light, and maybe new more vertical railings. I agree the bench should be removed and some vertical planters added in that space.