He was on the roof though? Depending on how he inspected, he may have lifted shingles and been able to tell from edges. Also, you dont say how much he is replacing. If he' really replacing (as in all the wood layer), it doesnt matter if he matches what used to be there.
Thats reasonable. Best to tell him too. Oh, I'd get a second estimate and a 3rd .
The whole thing sounds dubious to me. Why would a contractor be delivering a pile of ply if they haven't even started the tear-off yet. It costs money and time to deliver and then remove uneeded material
I would not deal, or even talk, to a "contractor' that "happened to be in the area". Well maybe I would depending on the looks of the equipment and crew but it would only be to get a bid for comparing to other companies.
If you are in a high wind or seismic area, you may wish to consider going over all the T&G 1x with 1/2" plywood to improve the shear resistance of the roof. Of course, the wall sheathing would be more important to strengthen, but it is presumably not accessible.
At $45/sheet? You're pretty free with the guy's money. The house has been standing for 50 years, so there's little benefit to be gained from an extra layer of sheathing. I also don't like adding weight to a roof unnecessarily.
In the case of the neighbor's house (where the ply was delivered along with the shingles) my wife tells me that they had water damage to the bedroom ceilings due to the leaky roof. I can only assume that a more through inspection was done before the material was delivered and the work started. I won't know that until I've had a chance to speak to the neighbor.
Let me clarify something that you might have deduced by putting a couple of different things in this thread together, although maybe not.
Yes, he was "in the neighborhood" but he was also roofing a neighbor's house, a family we have known and liked for over 20 years. I've trusted the nieghbor's judgement on other things in the past, so I trust that he did his homework before hiring this particular roofer. I can't say for sure until I talk to him, but that's my guess.
So this wasn't just a "Hey Look - a roofer - let's get an estimate." It was more like "Hey that roofer's doing Richard's house - let's get an estimate."
And yes, regardless of what his crew and equipment looked like, this will be just one of at least 3 estimates I get.
Appearances can be deceiving. They definatley arrived with sheets of plywood at my place. Why? Because inspection already showed they would need some. The company I used does enough roof work to have a ready stock on hand so they brought what they thought they would need, then a few extra 'incase' (which we needed some of those few extra).
Always get multiple estimates but getting to see them at work on a neighbors house can give you a good idea of the work they do.
I would say one other thing. A contractor who does too many different types of jobs (all with one team) tends to not be very good at any of them. The fellow we used does roofs (has a special team for that), siding (has a separate special team), and custom windows (with a 3rd team). Each 'team' does just their own type of work and do it well.
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