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Insulation and ventilation in 1882 brick home w/ finished attic

Hello folks. I have a one story urban brick shotgun/flounder in Newport, Ky. Wide temperature swings (100F to -5F) and typically high humidity. I am replacing the roof that is presently a single layer of shingle over plywood. Although it is likely 40 years old, it is working fine, just shedding a fair amount of sand. We want to replace it before it fails. The attic space was finished at some point, likely the 30’s with plaster/drywall palced against the underside of the roof joists. I am aware of no insulation ever having been installed.

To my question. What would be the correct approach to insulating and venting the roof/attic? I have gotten a different opinion from every roofer I have had over for quotes.

My options as I see it so far are:

 Istall the new roof with all of the attendant underlayment, flashing ,valleys etc., but no venting, and call it good. I mean the roof has lasted a very long time with no venting and no issues. The downside is I really would like the space to be cooler in the summer and warmer in the winter if I can achieve this without causing issues to the roof.

  Install the new roof with intake vents and box vents/ridge vents, and not insulate at all. Mainly for fear of creating moisture issues. This feels like it would work well in the summer to keep things cooler, but not sure if it would affect the winter inside temperatures. Plus, this has the benefit of addressing the cool roof/ice damming issues I keep reading about, but honestly don’t know if have ever been an issue on my house.

   Attempt some sort of insulation along with the properly installed and vented roof.

Any advice/help would be greatly appreciated. Keep in mind that this is a late 19th century brick home with ablsolutely no modern moisture barrier systems or insulation, and it has survived well regardless. Thanks for your time.


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