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I got into a project this weekend that involved removing the siding and getting into my wall from the exterior to fix a plumbing leak. Upon doing so, I noticed much of the framing wood above the plumbing leak was wet.

For reference, the house has blue vinyl siding that was added without removing the previous (and likely original siding) from the 1950s. See the yellow old siding and blue vinyl corner:

enter image description here

I have two concerns:

Concern 1.) I am concerned that water is draining behind the fascia, thus soaking the fascia board and the wood behind it. My reasoning is due to a slight gap behind both the gutter and in-between the fascia and fascia-board. In reference to a comment from another stack exchange post (Roof Gutter Installation), a comment said that sometimes a gap is okay to provide airflow, but often times roofing material does not extend far enough for this to happen. See the labeled image below:

enter image description here

where:

1 = not much lip from roof material

2 = gap behind gutter

3 = gap between fascia and fascia board

Concern 2.) There seems to be a continuous line of water leaking between the gutter and the fascia:

enter image description here

My thought was that this continuous drip was dripping between the new vinyl and the old wooden siding, which was then not properly draining when reaching the window beneath it:

enter image description here

I am planning to re-side this portion of my house, and I'm wondering if the gutter needs replacing. What is going on with this gutter? It was likely installed when the vinyl siding was installed. To me, it seems like it was not installed properly from the start, likely due to the vinyl siding being added on top of the old wooden siding.

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    It's very common to leave old siding on and installing new over the top, though it can make for an uneven surface. There aren't a lot of pictures of the gutter installation, so it's hard to say if it was installed properly or not. Get up on a ladder and take a look from above, not below.
    – FreeMan
    Commented Apr 26, 2022 at 12:15

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