We roofed this house in 1999 and again a year later when the insurance company pronounced hail damage. That was after finding shattered bricks all over the roof from a lightning strike.
So, we quickly went to two layers of asphalt shingles. Then, just short of two years ago, due to a change in agent of record with the insurance company. They re-assess the policy and values. Took pictures. We knew we were going to need to put a new roof on within a couple years. The insurance company said do it by the renewal date or they would drop us. There was a little curl to the shingles. I've seen much, much worst.
So I started getting the contractors coming by and giving their pitches. Usual number of depressing conversations. Some outright crooks. Weeded them down to two I thought I could trust. We put a steel roof on with a 40 year warranty. The contractor went the extra mile for us and worked to make sure the old roof was as sound and flat as possible before putting on the steel.
Same contractor, local fellow, also removed the old vinyl siding and put on new vinyl siding. Handled all the necessary changes in the way things are down now compared to 40+ years ago. Wrapped the house in a wrap designed for the purpose before siding. Arranged some outdoor electrical work at the same time. Security lights and outlets.
We are pleased. Had new gutters done same time. Not a very steep roof. But I would recommend getting something to stop snow from sliding, At least over the doors and walkways. A steel roof mounts to a wood framework mounted to your existing roof. The noise in a hard rain is less than before.