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Most roofing companies now have ladders that have a built in lift so you don't have to carry the shingles up the ladder anymore, but if I were to do a DIY roofing project, I'd rent one of those tow behind manlifts from Home Depot.Had my roof replaced last Spring ... two story house.
Watchin those Messican dewds hump all those shingles up that rickety, long ladder was quite impressive. I got exhausted just watchin that.