I love olive, it looks good year round, whether trees are in bloom, autumn color, or against snow. That said, my only concern would be that you don't go too dark. . Tribbix' Mountain Moss does seem nice. I have used Bennington Gray, which is sometimes cream and sometimes slightly olive greenish, depending on the light. You might want to look at Providence Olive, too. My two picks look far less green, in isolation, than does the Moss, but I think that when you put them next to the brick the green comes forward. Both of them change a lot throughout the day. We used SW fireweed for the clapboards, SW ripe olive for door and shutters, and BM compatible cream for the windows and other trim. So you know I love your color scheme.

Its not just esthetics, its breathability of the paint so moisture isn't trapped - you need expert advice and the right products or may be creating a never ending mess of peeling paint... which may indeed affect resale value. There are masonry stains and such but unless the brick is seriously out of sync with the stone (hard to tell on my monitor) I'd leave well enough alone. Actually - my inclination is to continue the stone up to the second story/roofline on the left side and really embrace the ancient stone village look you've got going there! (as someone who loves stone & old English villages that are made of it.)

Hey you are right I think you should lighten your brick it looks better and is timeless and will bring it more up to date but I think you should lime wash it romabio has many different lime washes and natural masonry paints it allows your brick to breath and looks beautiful and it will age beautiful as well

"Ideally, a primary or entry walkway should be at least 48" wide and even wider is [often] better." I concur 100%. Another consideration in addition to sheer usability, is that a walk's width needs to coordinate with the building architecture ... size being one of those characteristics. This walk does that in that it is equal to the full width of the opening at the porch. My guess is that the walk is 5' 4". I have no arbitrary opposition to straight walks, thinking that many of them are equal to curved walks in their potential to be beautiful. From what we are shown in the picture, either seems like it could work well. It would probably only be worth the expense of changing it if a person developed a compulsion about it, as compulsions cannot be explained by reason alone.