I lived that experience. In '72 I had Certanteed 30 year shingles put on a new 2nd story urban home and when I sold it in 2005, there was no issue about the roof. Never leaked, not leaking then, all shingles in place, with decent grit covering. So I had the same brand 30 year put on this new rural home and in about 10 years they started curling, fracturing, but not leaking yet. I agree with others that a good looking newer roof sells the house but there is a limit somewhere to providing some one else a bargain when you have the buyer, real estate agent, lender and occasionally the inspectors working against one's pocket book.
Yes I am having a steel "shingle" quoted, probably with the revered, pricey standing seam metal.
This roof will be a highly visible "curb appeal" on this particular house and it will look like yet another machine shed, pole building or "tarted"-up old house....not that attractive IMO I might just put aside some money for a new roof for the buyer, that way I will kill two birds with one bale of hay....giving them essentially the money down to buy...if only I could keep that cash away from the real estate agents take..we would both win.