The typical homeowner doesn't spend any time on their roof, and even if you happen to be a rock climber or a skydiver and you are already comfortable with heights, traversing a roof is an entirely different animal. The moral of all this is that being on a roof, has an element of danger that is not often considered. Gusts of wind can come out of nowhere, and if you are carrying an OSB panel or something similar, you will likely find yourself on the ground and in pain.
After you have considered your ability and quelled your fear of being on a roof, you now need to consider the task at hand. Roofing is a lot like making a milkshake: there are not that many ingredients, and the chore itself seems simple, but to make a really good one, you need to know what you are doing. This metaphor breaks down in that if you make a bad milkshake you don't have to drink it, but if you do a bad job of putting on a roof, you will have to live with it year round.
My main concern with any do-it-yourself (DIY) project is whether or not I can live with it if I do a less than perfect job. Painting is the easiest and most often attempted DIY project, and kitchen remodeling is the least often. Roofing has to be somewhere here in the middle. Whether it is closer to kitchen remodeling or closer to painting depends on how much experience you have with roofing.
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If you absolutely need a new roof to lower your energy bills and keep water and wind out of your house, but you absolutely cannot afford it, talk to a professional roofer. I'm a firm believer in doing some of the work yourself. If a tiling pro was coming to redo my floors, I would rip up the old floor before he arrived. With roofing, talk with your roofing pro to see if he will allow you to tear out the old roof for a discount on his cost. Some roofers are so busy during the summer that they are happy to have you do some of this work.
Professional roofing contractors still need to install the new roof, whatever roofing material it happens to be. Installing a new roof yourself is not something I would encourage. If you are handy and have some roofing knowledge, then most likely you don't even need to read this article. But if you are considering whether or not you can do this, you absolutely can. Tearing out the old roof is just muscle and sweat. Applying the new roof requires a little more skill, and it needs to be done quickly so that your roof is not vulnerable to the elements. This in combination with the danger of being on a roof, makes this a tough task for those who have little experience with roofing.