Something that is proven to last, won't fly off, easy to put on. House roof was steep enough, now the barn needs a roof. Don't want to do it because of the height, but would give it a try if I have something "other" than shingles that goes on quick, easy and lasts and lasts and lasts and lasts....

Hello, Quick question for the group... I have a 25 year old home with the original SHAKE roofing material on it. I do not have any leaks at this time, however, I know that it is just a matter of time before I do have an issue. For this reason and the fact that in California, insurance companies dont want this roof on your home, I want to replace it. Since the roof isnt leaking, I can do this at any time. I have heard people say that you can get better pricing during different times of the year. Is there any truth to this?? If so, what time of the year would I get the best pricing?? Final question is on gutter treatment. The house currently does not have gutters. I have received some quotes for 88 ft. of 7 inch gutters for $650 bucks installed... however, I am considering doing that part myself. The question is, is it worth the hassle, or am I better off just letting the "pro's" do there thing with the gutters! Thanks, Ron