When I did my own roof, I ended up with rooftop delivery: BEST MOVE EVER!!!!!!
I was supposed to be on the roof "catching" as 2 guys down below threw bundles on a truck mounted conveyer belt extender arm on the truck. I am big and pretty strong and thought it would be no problem, but it quickly became obvious that I couldn't keep up. The young guy on the truck jumped on the conveyer belt thing, squatted down and rode it up to the roof (single gutsy-est/stupidest thing I have seen in the last few years, as the tip of my roof, where they were delivering is about
27 feet up, and he squatted on the 12" wide conveyer belt!) Anyway he helped "catch", easily doubling my work output.
I can't remember specifics, I think rooftop delivery was included in price, I did slip guy on top a $20 when guy on bottom was not looking. Later with both worker present, I tipped another $20. Thought being, old guy on bottom was clearly crew boss and other guy was doing almost all the work, and I expected the whole crew to spilt the "open"$20, but I wanted other guy to get the other $20 to himself, as he really put himself out to cheerfully help me, and I didn't want to force him to share his $20. He may have shared with older guy later, or he may have kept it, I don't know, I left it up to him.
bottom line, order rooftop delivery, and have a couple of 20's. I am not usually a "tipper" kind of guy, but that was the best $40 I ever spent, I would have been in the weeds without their help.
If you order from non-Home Depot roof supply company they will pretty much assume rooftop delivery, as that is how the pro's operate. I think I nievely planned on hauling up to roof myself, and only changed plans when it was clear rooftop delivery was S.O.P. and would not cost me extra. obviosly ask to be sure... I was just lucky, had I had them delivered to the driveway I suspect I would have killed myself getting
14 squares of architectural shingles up the ladder, I was insane to have thought I could do it.