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I have an old ranch built in the 50's. It needs a new roof, insulation (currently no insulation) in the attic, and new gutters. It's almost impossible to find a good contractor that does it all. What order should I do the upgrades? I've heard gutters must be made to work with roof. I guess roof->gutters?? I might need to add more ventilation to the roof for the insulation. I'm guessing roof->gutters->insulation?? Thanks in advance for any help.

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You want to do the roof before the gutters. Gutters attach to the roof decking and/or the fascia so if you did them first, they'd have to be removed. If the additional venting you mentioned is going to be installed on the roof, turbines, etc., they go in afterwards or possibly along with the new roof. If the venting will be installed in the eave with soffits, that can be done afterwards. Last but not least, the insulation goes in after everything else is complete

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