Looking at the picture below, it shouldn't be hard for anyone to see that this is a bad design. On first glance it might all make visual sense but it is sort of like an Escher optical illusion. In the next picture the red arrow shows the flow of water and debris into the bottle-neck area.
The next picture shows the bottle-neck from above. Maintaining this area and the downspout free of debris will be essential to preventing serious damage to the roof and wall structures. This is a problem waiting to happen.
Sometimes my buyers will ask me for possible solutions to problems like this, and it is entertaining for me to look at possible ways it could have been done differently. This fix will require significant modifications----but not difficult modifications----to avoid a lifetime of pain-in-the-butt maintenance (all with the proper approvals of a structural engineer of course). If you compare this next picture with the first picture you can see where I have "overlaid" a design change that would eliminate the bottle-neck without "drastically" altering the "look" of the structure.
Although houses can come with a variety of problems---most problems have solutions that can be more easily remedied than the average homeowner can imagine. As an inspector I try to convey that to the buyer. When it comes to the house structure, it is all basically boards and nails ----it all comes down to whether the fix "pencils out" in the context of the purchase or not. It is rarely "rocket science."
PS, for those of you that are new to my blog (or for some other "unexplained" reason have never noticed) all pictures and smiley-face inserts (emoticons) have messages that show up when you point at them with your cursor.
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WA State, Home Inspector Advisory Licensing Board