I just had 95 years worth of roofing materials removed and a new roof applied by a local roofing company. Overall, I think they did a good job although I'm not knowledgable. However I did do some homework.
The house had skip sheathing, which is 1x4's, with around 4-6 inches space between boards. The skip sheathing was covered by wood shingles and there were several layers of asphalt shingles over that.
If any one is contemplating a complete tearoff such as I just had done to my 2 story 1925 footer with attic, I can highly recommend one thing - that you put down plastic in your attic before they do the tear off. The tear off is the very first thing they do, so have the plastic down before they arrive. You can use thin stuff, probably the 1 mil sheeting they have at Home Depot, etc. After the first day they'd done one side of the house and fortunately the roofers handed me a roll of such sheeting and I put it down on the other side before they tore that off. That will simplify cleaning of 1/2 the attic, but the first half is going to be pure hell. I already removed eight 5-gallon buckets full of debris and I'm sure I couldn't have removed more than 1/3 of the bigger debris from that 1/2 of the attic space. I figure the entire attic is around 1200 square feet. The smaller stuff is going to be even tougher - the stuff that's still too big for my shop vac. Add to that the fact that it gets harder and harder to crawl into the areas close to the eaves and I can see that it will be murder trying to get the attic clean.
I do have gable vents in north and south dormers (4 in all, 14" x 24") that I can temporarily remove and shove debris out onto the roof, followed by sweeping the sloped roof and cleaning out the gutters and doing pickup on the ground. That may beat continual bucket transport from the attic, but even so it's going to be a very tough job if I want my attic to be clean.
Even the part where I have plastic down is going to be hard. After I roll up the plastic and get it out of there (may not be easy) there will be a LOT of stuff close to the eaves, where I couldn't reach the plastic. That will be very hard to reach because of the very limited space in there. I'll have to resort to poles with some protuberance (like a hoe) to pull debris to where I can reach it. That followed by vacuuming with 2 extensions, hopefully. It's going to be messy, dirty work.
If anyone knows of any methods I can employ that I haven't thought of, I'd appreciate hearing about them.
Dan