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Your roof is a piece of cake, in terms of pitch. Very walkable. First you need to figure out how many layers are on there currently. If only one, you can go over with a second new layer. Given that this is not your 30 year home, that would be your best alternative. Otherwise it is a rip and re-roof, withice and water, and some plywood replacement. Depends on your issues.... I recall there were some undulating waves across your roof... Granules in gutter happens on a regular basis.
Start by figuring out the area in units of 100 sq ft. That is referred to as a square. Also want to figure your pitch. Get some local estimates. Some very good guys can do the estimate from the ground, but I prefer them to get up there and walk it. I have a couple guys that will come out to give you a price if you don't find someone you are comfortable with locally.
Gutters done afterwards. Need to consider the fascias before doing roof though. I have gutter company drop the gutter, cut to length at the site, with all the accessories.
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