There are very good reasons for the rule in most modern building codes that allows no more than three roofs on a building.
Having the right tools makes incredibly unpleasant tasks merely unpleasant. For ripping five or more layer of roofing off a 180ish year old house here is a good start:
flat bars similar to the stanley Wonderbar
spade forks out of high grade steel w/ash shafts and a d-handle
magnetic sweeper with a long mop handle and some Serious magnets
high power ratio tinsnips(or airframe shears)
hat
sunscreen
water bottles with the pop tops that you can open with your teeth
non skid nail buckets
industrial push brooms
20oz straight claw hammers
worm drive circular saw
lots of sheets of plywood and assorted 2x4's to make slides and funnels to the dumpster
high quality cordless drills
file to keep forks and flatbars sharp
Whatever your high school history teacher told you about nails being precious in the early 1800's in rural america was a bald faced lie. Those bastards nailed those cedar shakes on half inch centers.
If any one out there has a use for 70 or so pounds of 180 year old square nails in startlingly good condition let me know.
Walk carefully on 180 year old roof planking.
Asphalt shingles lose a lot of strength in August heat and sun. Sometimes this is good sometimes not.
If it's hot enough to melt shingles, drink lots lots of water.
