Great entertaining space! I'd put a lounge area in the sunken area in front of the fireplace. Then I'd keep dining outdoor furniture where you have it, but do a rectangular table. The iron table/chairs on the stone is kind of cold to me, so I'd try wood. I think light colored fabric cushions (kind of like the sofa) would make the stone look less heavy as well. The furniture in the mock-up is just kind of thrown together. Just trying to give an idea of what I'm referencing for placement.

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Thanks! The old dining set is not comfortable without cushions. I hate leaving cushions out because they get dirty fast, but such a process to bring them out and put them away. Plus our dogs are all over us so we typically clean up fairly quickly after eating. I hadn’t thought about it but the 36” height may help with the dogs. I think the bar height is too tall because of the dangling feet issue. They do make counter chairs with backs and that may be better than the backless. That’s a good point. The adirondacks are great because they are comfortable without cushions. Hoping this set will be the same. What color do you think would work best with the Adirondack chairs?

Yes, thank you Patricia! I am all for doing a different stool at the counter but my husband is adamant about them matching. Perhaps him hearing that a professional disagrees with him will convince him (though unlikely). I appreciate it!