Gutters!
Gutters are not the most scintillating of topics.
Yet they are vital in protecting a building.
A significant amount of damage was caused to the Cross House due to messed-up gutters and a lack of downspouts. I think…hope…I now have this under control.
I have had the same problem with the Carriage House and, a few years ago, was able to partially address the issue.
But all was still not right.

A huge issue was in the NW corner. Note the gutter to the left. Note the lack of same to the right. And that small overhang was A PROBLEM. Water had destroyed the trim below, and had even caused the plaster inside to fail.

Today. I had the gutter extended across the fill width, with a ‘dam’ placed at the very far right right to funnel water into the gutter. Yes, the gutter in front of the dormer looks weird but I plan to remove the dormer this year. It is not original.

There was a gutter over to the far right but not to each side of the small dormer. Water though cascaded down those narrow eaves, causing damage to everything below.

Today, a full-width gutter fixes the long-term problem. The small dormer (not original) will also be removed this year.

At the back of the Carriage House is a gutter/downspout I previously installed. But, well, it looks awful. Soon though, soon, it will look better.
I will deny ever stating this but sometimes protection outweighs beauty.
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They may look a little unorthodox but they will get the job done in the interim. There are worse things that could annoy then gutters across the dormers. You do what you have to do.
For the first time I can imagine the Carriage House without the extra dormers. It’s going to be beautiful!
I agree! It will make the front face look much more calm and coherent.
Protection allows beauty to continue. Too many times houses are built for flash that wears quickly.
I like seeing that you do all possible to keep the beauty intact.
Well done! These will hopefully manage the water flow, and keep water outside the Cross House.