Thank you for the mockup! That actually helps quite a bit...as well as perusing Houzz and Zillow Digs. I have realized that this set may be solid wood and a decent deal, but I think I would prefer something else. I actually find myself drawn to round table, which likely wouldn't fit my rectangular room, but that is another topic altogether! A piece of glass (which I can get in any size and shape I choose), a rug, and focus on accessories will likely do a lot more for the room than a "nice" table set that doesn't really suit me. Thanks for all the feedback.

I think it'll be fine, especially if you're careful about the finish. Your house is pretty much now, and so is the style kitchen you've pictured, and the wide arch. The word "transitional" is overworked, but generally fits anything that has past elements in today's design framework, and that's really what you have pictured. The word "Shaker" applies to the simple recessed panel, not the minimalist design philosophy here. The woods in your picture of the stairs are honey colored (medium golden brown) and in your kitchen drawing they're more spice (medium-dark orange brown). Since you're opening up your house rather than separating off the kitchen, I'd be more concerned with making the woods work together than the cabinet style (which by being so simple should go with anything). Just make sure you're happy with the choice you make! There's no point starting otherwise.

Beautiful room! I love the combination seating you have but if you decide to not use the bench for some reason then I would suggest 2 more black Windsor side chairs and just use the parsons at the head and foot of the table. I have white upholstered chairs at the head and foot of my RH salvaged pine trestle table and wood side chairs with slips only on the seats. I love this look - the linen slips are a nice, soft contrast to the rustic table. I was also considering black Windsor side chairs for my table but wasn't sure and then found my chairs on sale at Shabby Chic. I fell in love with them because they're so pretty but DH is not a fan due to comfort. He would have preferred the Windsor chairs. Looking at your photos, I can see they would have looked great! Can you share where you found your sign and clock hanging on the walls? I need to find some interesting wall decor!

I would choose very simple end chairs because the ones on the sides already have a lot of detail. Please do remove the dated, fussy curtains; they by themselves ruin this beautiful room. The side chairs look rather hard and uncomfortable. Perhaps you can have something done to the seats to remedy that. A beautiful rug will also soften the room and make it look much more comfortable.