We've had three hailstorms in the last month or two, so insurance is paying for a new roof! We really needed one anyway, so this is quite a blessing. The house was a foreclosure when we bought it, so it was a great deal but there was no info on the age of the roof, which seems to be much past its prime.
Since the opportunity has presented itself, I'm thinking of going with a darker brown shingle. I like the body color of the house, but I've never cared for the taupey-gray trim. I would love to paint just the trim someday, but I don't really know if that will ever happen. But insurance is paying for new gutters, which they will paint as well, so now would be a good time! I might have time this fall to get the trim painted, but I'd have to commit for sure if I have the gutters done now. Decisions, decisions!
I think a woodsy brown roof would still leave me lots of trim options. An online friend did some Photoshop for me; the third picture is a close up of the house with rich brown architectural shingle and Jamesboro Gold trim. What do you think?