I've always hired it done, or watched someone else do it. Observations from those times...
@JD Martin has some good advice, especially about using a jack/elevator/lift. Remember, each package of shingles weighs something like 70 to 90 pounds. You may be able to rent a ladder that comes with a lift sled on it - you put some shingles on the sled, stand on the ground, and pull a rope.
When I had the roof on my residence done, the shingles showed up the day before the roofers came. A flatbed truck from the roofing supply company, with two guys and an articulated conveyor belt, appeared in my driveway. One guy rode the conveyor belt to the roof (OSHA? Never heard of 'em) and then stood on the roof. The other guy stood on the flatbed and loaded bundles of shingles on the belt, which the guy on the roof took off and stacked. They moved the belt a couple of times to distribute the shingles around the roof. When they were done, the roof guy rode the conveyor back down, I signed the delivery sheet, and that was that.
If you're doing the tearoff yourself, you'll need to rent a dumpster. Usually you get an open-topped dumpster and put it in the driveway or maybe along the street. Ask the dumpster company what size you need, based on either the square feet or roofing squares - they will be familiar with this. Before you call, you might need to get on a ladder and (gently) check a corner or an edge - sometimes a new roof gets installed over an existing roof, so you might have two layers of shingles. Ask the dumpster company how much weight comes "for free" with the dumpster, and what the cost per ton is for going over that weight. If you're having the roofers come in after you do the tearoff, make sure the dumpster is there for them as well... they'll have cut pieces of new shingles and similar stuff to get rid of.
I have also seen a couple of dumpster companies that offer a lower rate if all you're putting in it is shingles, no general trash - I suspect they are hauling it to either a recycling plant or a construction and demolition landfill, which is cheaper for them than a general-purpose landfill. If you get a deal like this, and you hire roofers, you may need to check the dumpster before you call to get it hauled off to make sure it's only got shingles in it. On the other hand, if you also have some interior demo to do, it may be cheaper to pay the higher "garbage is OK" price for the dumpster and just rent it once.
I would plan on new flashing around the plumbing vents. Bright aluminum is always available, but if you look around a little, you can probably also get dark brown or black, if that matches your shingles better. For the plumbing you can usually get a one-piece boot that slides down over the top of the pipe. If the electric service comes through the roof, you can get a split boot that can be installed around the conduit, so you don't have to have the wires disconnected.
If there are vents on the roof, you might think about replacing them as well. Again, you can always get silver, and sometimes you can get darker ones to match the shingles.
I've had a roofer offer to paint the exposed part of the vent pipes to match the new shingles. If the pipes are metal, this works. If they're plastic, it'll work for a while, but PVC and ABS are hard to get paint to stick to on a long-term basis.
If there's a satellite dish on the roof, you may have to disconnect it temporarily while roofing. If the house is occupied, make sure the tenants know that their TV will be out for a little while.
If you hire roofers, they should make some effort to sweep up the driveway and maybe rake the yard when they finish. However, if you go around after they're done, you will always find more nails and bits of shingles and stuff. Try to look when that part of the yard is in the sun. Put an old hard drive magnet on the end of a 1x2 and swing it through the yard, or get one of those fancy magnetic rollers from the hardware store. The tire or lawnmower blade you save may be your own!
Try not to fall off. :D If you're going to be working alone, and if the tenants are home or there are neighbors at home nearby, hollering for help if you fall off is a time-honored plan. If you're all alone, you might arrange for somebody to call you every hour or two, to make sure you're not lying in a heap in the yard.
I hope this helps!