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ask about such mundane things as decking, felt, flashing and drip edge. Also familiarize yourself with the concept of the Square.
On decking: I prefer they replace it all. They'll want to replace only the pieces that are bad, but consider: if your house is 40 years old, every piece of decking up there is probably 40 years old. It's best to rip all of it off at once, replace it all with plywood (no fucking OSB, please, I hate that shit with a passion because it's glued-together wood chips) that's got sheathing clips between the sheets, and be done with it.
On felt: architectural shingles need 30-pound felt under them. Three-tab shingles are fine with 15-pound felt, but the 30-pound gives the architectural shingle a much nicer place to lay.
On flashing and drip edge: Drip edge is made to channel water into gutters. It has a little raised lip. Roof edge is made to protect the edge of the sheathing across the bottom edge of the roof. It looks like a piece of angle iron. If you put drip edge where roof edge goes, water will pool there and rot the edge of your sheathing. I probably run into three professional roofers a week who either don't know or didn't know until they ran into me that drip edge at the bottom of the roof is bad.
The other flashing I know you'll need is the Boot. These go around your chimneys, vent pipes and other plumbing sticking out of your roof. These come in galvanized steel and hard plastic. Ask your roofer which he likes and get those; both of them are reliable.
You might need step flashing, valley roll, all sorts of other things that I can't name without seeing the roof system. But whatever you do, don't reuse your old flashing. New roofs with old flashing look like you got cheap on us.
There is also a "leak protector." Everyone makes this but GAF calls theirs WeatherWatch, so we'll use that term. It's kind of a rubberized border. You put it on top of the felt along every edge of the roof, in all the valleys you have, and centered on the ridge. This keeps water from seeping in along the edges. Whether I'd use this depends on how much rain the area got. In Seattle, most definitely I'd use this...actually, in Seattle they recommend LeatherDeck, which is the west-coast version of WeatherWatch. In Arizona, save your money.
On ridge vent: There are three kinds. One is made of metal and stands alone--you don't (in fact, I think you can't) put shingles on it. Some people use it on homes, but it's kinda ugly. On sheds it's great. One is a rigid plastic, the other looks like rolled-up foot-wide Scotchbrite scouring pad, and both of them need shingles installed over them. Either one works, but before you sign a contract with a roofer make sure he'll run this the entire length of the roof. Some guys only run this the length of the slot. That works, but aesthetically it's not so good: ridge vent is about an inch thick. The slot is in the middle of the roof. If you've got 50 feet of roof and 40 feet of slot covered in ridge vent, you'll have an inch-high step five feet from each end of the roof. If you run ridge vent all the way down the roof, you'll have a nice straight line across the roof. It just looks a lot better. The best ridge vent to use is the one your roofer likes. They work equally well and they're priced about the same, but guys get attached to one kind and don't like to install the other. Brand here is pretty much immaterial: so long as all of the ridge vent on your roof is the same brand, it doesn't matter what brand you get because they're all reliable.
Now for the concept of the Square. It is a construction term meaning 100 square feet. You'll use it when talking about felt (a roll of 15-pound felt covers 4 square, a roll of 30-pound felt covers 2 square), shingles and maybe roof decking. You won't use it when talking about ridge shingles--those come in packages that cover 20 linear feet of ridge. I mention this because if you have a 1900-square-foot house with a moderately-sloped roof and the guy says you need 70 square of shingles, you know he's trying to rip you off. I don't care if you live in the House of the Seven Gables, you cannot fit 7000 square feet of roofing on a 1900-square-foot house! On the other hand, if he comes up with an estimate for 25 square, I don't think he's trying to cheat you. A 1900sf house has more than 1900sf of roof--part of it hangs over the sides of the house, part is taken up by the slope, if you're using three-tab shingles part of this is going to be starter strip and ridge cap. And if you have an attached garage...you get the idea.
How do squares translate to bundles? Several bundles comprise a square because shingles are heavy and have to be carried up ladders. In the GAF line, Sentinel and Royal Sovereign three-tab and Timberline 30 are three bundles per square, Timberline 40 and Timberline Ultra are four per square, and the Premium Designer shingles are five to seven per square. I tell you this so that when the shingles are delivered--trust me, you do NOT want to drive to Home Depot and pick these up in your pickup! Yeah, it's cheaper to do it that way...but when you get 'em home, you have to unload these heavy-ass 100 lb/bundle shingles--and you start counting them, you won't get to 72 bundles of Timberline Ultras, notice that there's another whole skid of shingles sitting there for your 2500sf roof, and think "why am I getting too many shingles?"
Of course, there's the most important test: Walk behind the roofer's truck. If there's a Bush sticker or fifteen Jesus fish there, find someone else.
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