As I posted before I have tar paper on the sidewalls of my house thats been up for a month or two. Its been kind of beat up and now I’m ready to side the house. I’m putting 3/8 inch foam on the walls then siding with vinyl. Would it be ok to put another layer of tar paper right over the first as I side or would two layers be a problem? When I get to the windows which have been flashed with self stick membrane to the tar paper what should I do with the second layer. I know the self stick can’t be freed at the sill and jambs from the original tar paper so should I just go over it with the second layer and any moisture that does get there will run out over the first layer? Thanks. Also , I noticed that wood exposed to the weather for a while turns grey (even PT wood). Does this effect the wood structurally or is it just cosmetic. Thanks again.
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I'd consider applying the 2nd layer of paper on top of the backer board. As you install the vinyl, have the tar paper overlap the nailing flange of the vinyl so that any water that gets behind the vinyl will only have to travel 3' before it gets diverted from behind the siding.
As for the other situations, I'll let someone else chime in.