Some places you have to get a permit to re-shingle a roof, some places not.

Example if you have asphalt shingles and replacement is $10k (you may have tile with longer life and higher cost so works out to be close to same) at 20 years is $500/year or just over $40/month.  

If you find there are tons of missing shingles, tarps on houses and a bunch of folded up corners (Google Street maps can show some of that) then you know that there is not money being pushed into that neighborhood.

To me, it seems like all nail heads should be underneath the other shingles that overlap. 

He did and they told him that since we didn't change the foot print, no permit was required.In another municipality, they required a building permit for new shingles and a new furnace. 

DON'T go with the cheapest company to do the work- you'll pay for it later on down the road (missing shingles, peeling paint, wasted materials, etc.).

I have discovered an alternative to treat asphalt shingles to help us on the selling end in the future.

Ice damming is real and creates water intrusions, when the gutters start backing up with snow, the warm roof melts the snow, but it refreezes and expands getting under shingles, and then into roofs.

I have and continue to work on different CAP X Improvements, including new roof shingles, new windows, new sliding doors, landscaping, new appliances, and more.   

I lost hearing in my right ear due to shingles a couple months ago and I'm pushing off addressing that until I have free time so I'm certainly not going to rush over to pander to him.