Company A: $11,940.00, GAF Timberline Lifetime shingles. Gave estimate on the spot. Said job would take less than one day. Estimate includes $700 dumpster charge, and up to three sheets of plywood. (I estimate that the one soft spot is only 1 foot x 3 feet.) Cricket not discussed.)
Company B: $9,280, IKO Cambridge AR. Gave estimate on the spot. Said job would take less than one day. No dumpster; uses company-owned dump trucks. Up to three sheets of plywood free. If I want GAF shingles, they would charge an extra $980, bringing the total to $10,260. Price of building a cricket next to the chimney included.
Company C: $8,575, GAF Timberline Lifetime singles. Came to my house on Monday, promised an estimate via email in one or two days; it arrived today, four days later. Each sheet of plywood, $50. Will probably use a dumpster. Cricket included.
Peripheral stuff like ridge vents, drip edges and replacing plumbing pipe penetrations with non-rusting aluminum ones are the same with all three companies. The warranty on the IKO shingles seems better than on the GAF, but once you read them you see that all contain too many loopholes and limitations, and just about all shingle manufacturers are involved in class action lawsuits regarding not honoring their warranties.
In Company C's favor, aside from the price: He was the only one to walk on the roof, inspect it and tell me I really didn't need a new one; there are just portions of one or two shingles missing. Also, his email proposal was the most professional, with each item specified in great detail and everything neatly typed in a Word document.
Against Company C: He didn't meet his own deadline for the estimate, which raises doubt about his trustworthiness; the job would take more than the one day the other two companies promised, and the dumpster. (I probably shouldn't be concerned about the dumpster, as it will be on plywood "feet" to protect my blacktop driveway.)
As I am writing this, Company B called. I asked how C could be so much lower than B even with the GAF shingles he wants an extra $980 for. B called back at few minutes later, after checking his figures, and came back with $9,700 as his best price.
(For the record, HD charges about $100 per square (3 bundles) for the GAF Timberline Lifetime shingles, and my roof needs 34 bundles. IKO runs about $84 per bundle if picked up, $88.65 if delivered, and $90 if boomed up. IKO prices are from an Indiana company, ReeseWholesaler.com. So HD, a retailer, would charge $510 more for the GAFs.)
With C being $1,125 cheaper, seems like a no-brainer to chose them. But I thank you for your comments on something I may have overlooked, and whether to bring in a company D and E.