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I am remodeling a 1875 house. I have removed the deteriorated cedar siding and am putting on new sheathing, 1/4 fan fold board, taping seams, and then installing soffit, fascia, and vinyl siding. My main concern and issue comes with trimming out the existing windows. When putting the j-channel up against the window trim(wood 1x4's), the trim is either flush or inset from the j-Channel. There is also a sliding door that I need to work around. See pictures.

How should I proceed?

Should I build out the windows by adding an additional 1x4 to the existing trim, just caulk the joints between j-channel and inset existing trim, or is there another suggestion?

Thanks in advance.
 

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Somethings really wrong with that window install.
Did someone cover up the nailing fins with that new wood, or are they flat jamb replacement windows?
If there's a nailing fin it should have been sitting on top of the new sheathing, not recessed like that. No amount of caulkings going to stop it from leaking.
Why the fan fold if your going to install sheathing over the wall?
After removing that drip cap trim that trim around the door could be wrapped with coil stock and a piece of Z molding added over the door.
 

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I would fully agree, something is wrong with that install. The replacement mentioned with poor install is the sliding door. This house has undergone several additions over the last 100 years, and the previous owner(s) covered many issues that I am trying to resolve.

As to the sheathing and fan fold. I was not planning on installing sheathing. However, as I removed the cedar shakes I found that the majority of the home also has lap siding underneath, and that lap siding is nailed directly to the studs and is holding in the blown in insulation. Thus the need for sheathing on portions.

I am contemplating returning the fan fold and installing a wrap instead.
 
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