Shelter really isn't shelter until there's a roof. Roofing is one of the more rewarding parts of the building project---everything underneath is now protected from the elements, and you can get work done regardless of the weather. First you have to get the materials up there, though. I built a temporary stand-off since the roofing goes 3/8" past the drip edge, and put some stops so the ladder can't slide off. Then it's a matter of shoulder loading the bundles of shingles----3/4's of them weigh 68 pounds, and every fourth weighs 76 pounds. (one in four bundles has more shingles so it will work out to 4 bundles per square, a square being 100 square feet covered)
Hard to tell in the picture but it's 26' to the ground.
I made a work platform out of scrap to hold stuff. You need a flat surface to cut the shingles on. There's a specific pattern to cut each starter shingle, working left to right from the roof's edge---that way the seams don't overlap. Every 5 courses I snapped a chalkline to keep everything straight (or else when you get to the top everything looks un-even)
The valleys......This roof has every challenge there is---steep valleys, gable junctions, roof to wall junctions, even curved rooflines. I'm of the opinion there is only one correct way to roof valleys when using composition roofing, and that is to lace them. The cheap shortcut is to put metal flashing down and simply cut the shingles at the bottom of the valley. The metal tends to cook the shingles causing premature failure. The shingles are cut right where the water flows. Leaves and pine needles accumulate and get under. Other than chimneys, valleys are the most likely origin of leaks.
Three reasons roofers don't lace valleys----They don't know how (I exchanged free labor for an experienced roofer that DID know how for a roofing lesson) it uses up a lot more roofing material, and it takes more time.
This steep gable comes right up against the pop-out roof, creating a snow-trapping funnel. I put down this sticky sheet rubber stuff in the valley all the way up the sidewall, then flashed the vertical surfaces with lots of flashing.