Allow yourself plenty of time, and don't expect to have the whole crew for the whole time.
A day to do the tear-off, including pulling all the old nails. (If you don't pull the nails, you'll wreck a few shingles when your nailer hits old nails.) A day to prep the roof: Replace bad sheathing or completely re-sheath, underlayment and drip edge. Two days to lay down the shingles. Longer if there are valleys or other complications.
Sure, you can do it MUCH FASTER than that with four guys, but the results won't be pretty. Take your time and do it right. Make sure the sheathing is in good shape; otherwise put down a layer of of 7/16" OSB over it. Put down "ice dam" underlayment if your roof is subject to ice dams. Lay out vertical chalk lines to line up the shingles. If you put down the felt straight, you can use the lines on it to keep the shingles straight; otherwise use horizontal chalk lines.
You will save a lot of time if you use "architectural" shingles rather than three-tab. They're bigger and you don't have to be as careful as with three-tabs when you install them for them to look good.
Don't get in a hurry with those roofing nailers. Amateurs and many "professional" roofers will put the nails too high and miss the shingle under the one being nailed. If this happens, you won't know until the first storm comes.
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Today's Featured Article - Earthmaster Project Progress Just a little update on my Earthmaster......it's back from the dead! I pulled the head, and soaked the stuck valves with mystery oil overnight, re-installed the head, and bingo, the compression returned. But alas, my carb foiled me again, it would fire a second then flood out. After numerous dead ends for a replacement carb, I went to work fixing mine.I soldered new floats on the float arm, they came from an old motorcycle carb, replaced the packing on the throttle shaft with o-rings, cut new ga
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