I have never used Glidden but I have used Benjamin Moore's Saybrook Sage on two different properties. The colors look fairly similar on my monitor but you'd have to look at them in person to check on it. Both houses were older (1914 or so) and I received a lot of compliments on both. People would even knock on the door and ask for the color.

I love the colorful look in Capitola. I think what you like is a great combo but more navy than gray.

Couple comments: All front facing will be stationary windows - not to code, need ventilation and emergency egress board n batten gables - probably will not look very good, as the roof extends farther down the wall on the left than it does on the right (I believe the slopes are different for each side of the ridge). Having a band, with the change in siding, does not relate to anything on the left and there is also the bumpout in the wall footprint. It is also a more "classical" look, whereas this is more of a "modern" look (describing in basic terms). new horizontal lattice along the bottom - are you talking just replacing what's there, or more? If you do any vertical board&batten, that will counter against the strong lines of the slatwall (much more prominent with air gaps than horizontal Hardie siding will be)

Leaving the siding as is, paint the trim B.M. Wedding Veil. It is a nice off-white, so it won't be as harsh as a true white. It also will work well with the black roof. Paint the front door black: B.M. Deep Space. Again, if you want wood or a wood look go for a lighter tone.