Well, for the record, I’ll post what I offered this homeowner.
First, two bits of info I held back from my original post: 1) This was a previous customer for whom I had done several at-cost or heavily-discounted repairs in the past on other parts of the roof (he has previously had some long gaps without a job). 2) With the exception of 1 shingle, all the damage was on a fairly isolated plane of the roof, which was separated from the rest of the roof by one ridge, one hip-ridge, and the other two edges were a rake and an eave. This slope was the worst problem on the house, and was only 8 squares total.
Keeping in mind that on this roof, a full-house roof replacement would come in around $300+/square (before accessories), I told him that if he wanted to replace just this one isolated slope, I would do it for $400/square based on actual materials used, or $3200 estimate.
I also offered to replace the missing, visibly damaged, and invisibly damaged sections (areas of wind lift where nails were pulled through, but shingles had lain back down in place), and collateral damage from repair, estimated to be 4 squares or less, at $500/square (again, based on actual materials used, so estimated $2000 max).
Lastly, I gave him an option to replace the missing and visibly damaged portions, and re-nail the pulled-through areas (several good-sized such areas) rather than replace them (thus, no new material used), and (of course) replace any collateral damage from the repair. I estimated this to be no more than 2 squares, at $500/square on actual materials used, for a max of $1000.
These options would all include warranty on our new work.
In my book, any smaller repair than that would have been pointless, as there would be more shingles flying off before the month was out due to our windy spring thunderstorms and the poor original installation.
He declined my offers, obviously. It turns out that he called the contractor who built the house, got the number for the original roofers (this is the original roof), and they were the ones who came out and did some kind of fix for $125. These are the same guys who botched it so badly the first time, resulting in blow-offs and repairs every year. These guys are out of Fort Worth (50 miles away), and have been in business for about 20 years.
When I asked him about it afterward, he told me that he thought maybe I needed to figure out how the other roofers were able to keep their prices so low and still make a profit. We talked a little bit more, but I basically let it go after that comment.