While roofing is not a difficult job to complete, there are many intricacies to the trade that make a roof leak-proof. Read several books and resources before you begin and follow the manufacturers instructions for the roofing material.

Before you strip a roof, an appropriate sized dumpster should be placed as close to the house as possible to reduce the handling of the roofing material (Buy a tarp and cover your dumpster when it rains.  You will pay for the weight of the dumpster and you do not want that to include water.)

Nailing shingles with a hammer can be very tedious and sometimes damaging to your thumb, especially later in the day when you become tired.  Try borrowing a compressor and roofing nailer or rent one.  Before you rent it, be sure you are ready to nail.  The last thing you want to do is rent a nailer and have it sit in your driveway for half the day.

If you are going to attempt a roof for the first time, start with a shed or a garage. If it leaks, no big deal, it is not your kitchen.  

Leave the big jobs with lots of details to the pros. A professional can bring in a large crew and complete most jobs within a week. A new roof installed by profesisonals with insurance can be well worth the money.