I want to add that we may or may not use the shutters after the redo (yes, I know how the Houzz community feels about them😬), but if we do, we can certainly make the 2 sets on the front wider, to better suit the windows’ size. Our front porch has to look sort of bare from Nov-May because we get super high winds that literally blow everything all over the place, cover the porch with snow etc; we do dress it up a bit from May-late Oct.

I assume you will be removing all of the exterior siding, stone, shutters and window trim. I would simplify the exterior -- I like the second door you show (with the sidelights). The second entry door should be plainer -- a single door, possibly with windows at the top. I would choose a window design that complements the door design. Your current window design with transoms (?) over the main panels is not bad. Maybe single panels would look better though. I would also have bronze or black window frames, as you are planning. As for the siding, I would try something like reverse board-and batten where the "battens" are applied first and then the boards are put on top of those, spaced so that the batten is visible through a on-inch or so gap between the adjacent boards. It's a modern look that is not often used and is more appealing to me than is the common board-and-batten arrangement. It works best with wide boards -- at least 10" wide, and up to 12" wide and ones that are relatively thick -- 3/4" or 1" thick.

Thanks, nester44….I hadn’t thought of reverse board and batten, but I will mention it to my contractor. One thing that’s super important is this: whatever we do must be able to withstand the winds, because when it rains heavily and the wind blows just right (or wrong), we have water coming in; not always, but often enough. The overlapping vinyl siding is the worst, as the wind lifts up the panels slightly and blows the rain underneath them; our contractor thinks that properly installed and secured Smart Siding (or Hardie) will make a huge difference. We’ve addressed this issue several times already, but so far nothing has helped. All siding etc will of course be removed, and we also plan to improve insulation while we’re at it. The stone will stay, it is real and we like it. All the odd window surrounds (all plastic) will go….we hate those.

Good idea on the insulation. Two other thoughts -- depending on your budget. Select a new garage door that complements the front door in color and style. Or have a custom garage door made from the siding material with the same pattern as the siding. A paved driveway and entrance way would be really nice. If you do that, be sure the drainage issue is dealt with so that you don't end up with a flooded area near the front entryway.

Yes, the garage doors……I think for now we will have them painted in the new house color, but we’ll likely replace them in a couple of years. We love real wood, but many shy away from it because of our weather. So far, though, our cedar shutters have helped up well, so we’ll see. When we first started to look at houses up here hubby wouldn’t even consider anything w/o a paved driveway; today we feel differently. We might end up using some sort of paver product (or similar) with holes in it, but I doubt we will ever pave it….there are plenty of alternatives out there.

Rough vision with green siding

Driveway pavers are indeed nice. You'll get more permeation of rainwater into the soil and less cracking. A large driveway area with pavers would look very nice, as would a driveway composed of large cement "blocks" separated by 4 or 5" of river rocks which would allow water permeation.

Thanks, Celery! The roof will be a much darker metal roof (Burnished Slate), green will be less minty….this has been hard to figure out (color wise). I like that you edged the beds with larger rocks….much better. We’ve worked so much on this house over the last 7 1/2 years, mostly inside, but we’ll get to the outside eventually! One problem: can’t find anyone to do the work! 😩
First pic shows (upside down) the burnished slate of the roof, and I’m thinking siding maybe similar to the gray-green (Colony) in the second photo…..

Of course the colors look a bit different (darker) than IRL. 🤷‍♀️

I see :-))

Celery, you’re a magician 😉….thank you!