well you certainly have hi class issues. Personally I like it as is. The fridge wall maybe could be redone to get your select oven installed. Kids will grow and the interesting ?ledge won't block them when they are taller. Is it that critical to see their every move? What could they possibly be doing while seated in the chairs that is risky? Install a mirror angled properly above the bay windows to look at them . When you are cooking your back is to them anyway. The dark counters don't have that much impact if you ask me as the space is large and eclectic and the counter isn't a big player in the scheme. Its very nice: you are lucky.

Ha, thank you. Yes, it is a lovely space. We love the whole house.
However, we are a family of five who could use a second oven, for baking and holidays. I’m also not very tall and literally can’t see the kids when I’m on that side of the kitchen. I think it would open up the space.
But... I asked for opinions. Maybe the answer is do nothing?

I agree with your ideas about the island. The cabinets on top of the island would drive me crazy; they're so intrusive. Not sure that Quartz is the right material for your kitchen island. It could work if you choose carefully the right Quartz so that it is not too contemporary, and not incongruous with the rest of the kitchen, most especially not the Quartzes with the chunkier veins--I'd avoid those for your kitchen. What would go best is soapstone, or the granites that look like soapstone like Virginia Mist and Jet Mist. But you said you want to go lighter, and I realize soapstone or Virginia Mist/Jet Mist is not going lighter; I am just suggesting what would go with the rest of the kitchen.

Re the double oven - logistically you need a cabinet to hold it. Where are you putting this double oven, and where are you getting the cabinet? The space where the microwave is now? Is that an oven under the microwave? Do you need to add a double oven, or just add a single oven? The addition of the double oven might be a bigger undertaking than you realize.

I personally love those cubby holes on the counter at the sink . It’s not the main sink so interfering not issue / and they allow small plates ,spice jars , etc , millions of uses .

The plan for the double oven is to remove the lower oven (it’s 23 years old) and microwave and put a double unit in there (likely the Viking or Bluestar French door double). I think/hope it will fit in the space with minor modifications. We have a large pantry between the kitchen and dining room where the microwave can go. And plenty of storage for anything I’d house in the cubbies on the counter. Right now, they house mail and clutter.

Nice kitchen!

Definitely remove the cubbies on the island. I think wall oven (vs replacing the cooktop with a 48" range) is a great idea. The general consensus is to not put in a combo oven-micro b/c microwaves generally have a shorter life span and when it dies you'll have to replace the whole unit (unless I'm misreading what you mean by "double unit" - maybe you mean two ovens?)

Under the range - I might try to retrofit in some pull out drawers / trays. Much easier than having to lean down to reach for pots/pans in the back of the shelves (I'd also consider replacing the under-cooktop cabinets with proper drawer base units - I'd hate to have all my pots/pans etc just open... but then I'm a vigorous stirrer ;)