"Dilemma number one is right there as you walk in. The old style railing and bay window. Most living will probably go on in the family room further up front. What would make this a really attractive area that says wow when you enter?" I'm confused there. Is that the actual entry (I don't see a door). If that is an entry hall I'd treat it traditionally with a center table and put a lovely piece of glass or art on the center table. Hall tree and bench against the wall and a piece of art on the wall...treat it like a gallery but keep the scale small enough to move around easily. "Dilemma number two is the hall bedroom with the shelves. It will be occupied by a college friend for now. I doubt they have *that* many books to fill up two rows. The room is small, and I can't come up with a way to update and really make use of the space. It also has a chair rail, as does the adjoining small hall bedroom next door. " So far that appears to be the prettiest room in the house IMO. I wouldn't fill that with two rows of books...I'd use it for display of collectables and some books on a limited basis, lots of blank space as well. I'd paint the entire room in a soft and somewhat bright color to lighten it up. Maybe a soft celery green? I love the window and the shelves. "The last dilemma, at least for now is adding a breakfast bar or island to the kitchen, so there is a place for a quick coffee besides the gazebo. Would you place a small bar/island by the pillar and slightly obstruct the path to the dinette, or have a small work island plus put a small bistro near the french doors and visually block the entry to the family room from the kitchen." Whew those are challenging spaces. My first thought was to find out which walls are supporting and which can go. I'm assuming you want to do something less invasive. OK so here goes my lecture.... Some homes aren't suitable to breakfast bars or islands. The layout is wrong or the size isn't compatible. Forcing one in causes (in the words of sir toppum hat...my son's hero) confusion and delay. Actually it causes a traffic nightmare. You might have room to tuck a stool under the end of that little bar area, but that's it and to force one in isn't sensible really. I have two homes with no area sensible for island seating...suprisingly we've survived and learned to sit at a proper table :) It's not all bad. If you feel you must have this...and really I don't think it's a smart idea, I'd put a very small bistro table right smack in front of the doors to the outside, NOT in any of the other walkways. But honestly, I'd put a smaller table in the gazebo and a very small loveseat or a couple of soft chairs with a table off to one side of the gazebo for more casual coffee seating. It's going to be a fun space eventually, but you have your work cut out for you now. Take it slowly and you'll figure out how to live in the space :) Whatever you do, don't turn the gazebo into a pretend outdoor one with fake ferns, flowers on the walls, blah blah...I've seen it done and it's painful :oP

I really like the color you selected. It shows as a taupey or light sandy gray on my computer. And I really like it with the Hunter Green. Is the part you want to paint white the fascia trim just under the gutters? I just used a color called SW Dover White and just love it. It's really a light cream, but it's warm and very soft. Are there any other places that will be white?

Get an obscure window film like "blue chip" from a box store. It will let light in and keep it looking like a window without a view inside. (We have it on a bathroom window) I would not put anything black on or around the window, it will make it look like you are missing glass.

Yep I'd recommend getting rid of the bow window. Very pleasant house. I like the sage with the brick, but charcoal gray is also and option for your trim.