I like both Rebunky's and MG's ideas. If you don't want a full banquette, you could still have a window seat and then a dining room table. We had a Craftsman home once and, in addition to dividers between dining and living similar to what MG shared, we had a window seat in the dining room plus wainscot in the dining area in Craftsman-style (not beadboard) with nice, wide moldings at the top to create the plate rail. That and your trim on your doors/windows should easily keep the Craftsman details you love. Of course, I realize that all Craftsman moldings probably aren't the same but we were able to recreate our moldings in a family room addition using various pieces of readily available moldings from HD. I would just add that, imho, if you end up having the w/d in the kitchen, I really don't see the problem with that. I wish I had a picture to share but I someone who has a w/d, side by side, not stacked, in their kitchen behind bookcase doors built on strong piano hinges. The door glide easily and she had some books and pretties displayed. Most of the pretties had museum gel to help hold them in place. She does laundry regularly so the clothes are loaded, washed, folded and put away without laundry piling up. Without a laundry room, you would need to do that in order to not create a mess area. If that's your style, it could work well for you.

I guess I should have mentioned there's a fireplace on the all brick wall of the living room on the far side of the living room, and the current entrance has a partial (3/4 height) wall/bookcase to separate it from the family room.

@Patricia, you have a good point. I think I will definitely want to consult a designer to get their perspective from an aesthetics/space usage mindset. I do have a large media room in the lower level where my big screen is, so I figure if I ever have a large group to watch a game, etc., that is likely where I will need the most seating. The upstairs could then be used more generally for entertaining. My dining table seats 10 and moving it into living area would allow me to add chairs on either end. The addition of a 9-10’ Island would add seating as well. At worst, the family in its current footprint could snugly fit a ~6-7 person sectional and a chair. I think with an additional ~2-3’ feet in length and width, I should easily be able to fit a sectional in there as well as 1-2 accent chairs. Plus if I’m entertaining there would be plenty of space to gather at the end of the kitchen where the new bar would be. These pictures are not by any means exactly what I would do (I used a trial version and stock colors/cabinets), but should help give a sense of layout.

Your request for help is quite broad and without a lot of specifics. That makes it hard to answer. I'd suggest breaking it down for yourself and for us like this: 1) Before you start choosing finishes, you'll want to solidify your kitchen and likely furniture layout/orientation. You'll get the most help with that if you post a current floor plan of this entire floor drawn to scale with measurements noted on. Your architect might already have a floor plan you can share here, or you could make one with a tape measure and some graph paper. Generally a 1 square = 1 foot or 1 square = 6 inches is a good, usable scale. Please indicate on the plan which sections of which walls are coming down and any other features (good/bad views out certain windows, fireplace, ducting that can't be moved, etc.). Also note anything you'd particularly like to achieve layout-wise (e.g., an island, a view from the island to the TV, etc.). Post that and and people will have enough information to make helpful suggestions. 2) While you're fielding suggestions about your layout, sift through Houzz and Pinterest to find some inspiration pictures you like. Look for rooms that really sing to you and have the kind of appearance or feel you really enjoy in a home and want to achieve here. Once you have found, say, six or more pictures like that, post all of them together on here and ask people to help you review the images and figure out what the commonalities between the pictures are. This will help you identify what specific things you really respond to so you can include those deliberately in your new spaces. 3) After you can articulate what it is your really like and want to bring to this space, THEN repost this question about colors choices and finishes with that information. Provide your final floor plan (the result of #1), explain what specific finishes you like or what you're specifically trying to achieve through finishes (the result of #2), and then ask us how we'd achieve those stylistic preferences in this space that you have planned. You'll get MUCH more targeted, helpful help. Only then will people understand your taste and the space that we've got to work with. THEN they can say helpful things like, "You might like X paint on Y surface with Q backsplash, plus maybe G feature on M wall? That takes advantage of your space for K reasons while adhering to your taste." Also, some side notes: a) I think you'll have an easier time balancing the dining set with styles you prefer if you break up the set across several different rooms. Use the table in the office, the chairs in the dining room, and the hutch in the kitchen or whatever. With all three - the hutch, table, and chairs - together in the dining room (and being the only furniture in that room), the country note you don't seem to be a fan of will inevitably dominate that room. b) I disagree with Sophie that it makes sense to hire an interior designer at this time. When you bring in a professional, you want to have some idea of what you're asking them for. Something you want them to help you achieve. I don't think you have that yet, and free discussion here is a good way to pin down your own thoughts a bit more. c) I don't think whoever said this looked like an inexpensive house meant it in a denigrating way. You mentioned several very large ticket items (kitchen reno and opening up two separate stories of your house), and I think she/he was simply trying to make sure you're not putting more into the house than you can get back when you sell. That can be devastating. But in case that made you feel weird about having posted, rest assured that people post on here with every single kind of house. Is this the grandest house we've ever seen? No. Is it the humblest? Also no. But no one cares. We're all just here because we like improving homes. The starting point really doesn't matter.