Re: Tips on roof tear off and reshingle
First off, you're going to want to wait for all that snow to melt off.
As DJ said, put the dumpster in the driveway and pack the debris. A wheelbarrow will work, but hand carrying will be just as fast, especially with help, and ultimately easier than trying to control and work with a wheelbarrow on a sloped surface.
That is a very easy roof to work with, a pro could have it stripped and relaid in about two days, so you should be able to wrap it up in about a week, barring any sheathing or framing repairs.
Any flashings with a rubber grommet in them (all plumbing vents ), replace with new, most metal flashings (exhaust vents, chimney jacks, step flashings ) can be reused. Use care removing the roofing around the chimney flashing, as long as you don't damage it and it is in good condition, it can be reused as well. Use care around the step flashing at the roof/wall transition, it can be reused as well, and, it doesn't have to be fully removed with the old roof, just carefully remove the old roofing.
Ideally, You would look for a weather window of at least a week so that you could strip the roof and have it stacked by the supplier, less handling for you. In lieu of that, at least peel the ridgeline and get the new materials delivered, then continue with stripping and weather proofing your roof. Have plenty of tarps handy if you're working in volatile weather conditions.
I suffer from CDO ... Its like OCD, but in alphabetical order, LIKE IT SHOULD BE!!!