Shingling roofs on new construction when I was probably between 17-21 years old. Most of the roofs were 12-12 or 14-12 pitch everything had to be handnailed on steeper than a 12on12 slope. Try climbing up a ladder and up toe boards with 65lbs on your back in july all day everyday. Think ive got the back of a 60 year old man from it and im still in my 30s.we did a couple 16 on 12 pitch roofs it was like working up a wall on doubled up toeboards. We got paid $20-$35 a square (three bundles of shingles) so wasnt no riding the clock if you didnt nail on you didnt get paid. Sometimes wed spend a day prepping and stocking out yhe roof tgen it would rain the rest of the week so we dint get a check at all but it was good money if you were willing to put in the work i could hand nail around 7-8 squares a day at the time