ok,,so lets start w/the kitchen. well, paint colors actually. it's ok to do different colors in other rooms,,,if you can see both rooms, slightly, then either do the same or do similar coordinating tones. The rest of the advice is if you plan on keeping what's there. If you're going to rip it out and get a new kitchen in a year, then live w/it if you can. If this is all you can do for many years, then see if the changes, below, are something you can do. if you plan on keeping all of that wood trim (if it was me, I'd prob paint every thing except the beams on the ceiling, and maybe the trim going up the staircase. In the kitchen you have so many dark and heavy elements, I feel you need to lighten it up. I can live w/the black tile, for now, but that brick? hell no. that has to get painted. You can paint the brick on the island, or, I'd cover it up w/panels/trim and paint it a soft charcoal to match the floor (or whatever color you like) Grab some thin wood or mdf panels from HD or lowes and cut to fit the 3 sides. Use construction adhesive to adhere to bricks (or get some masonry screws and screw them in) then get some 1x2 primed trim pieces and secure all around the borders..like so if you want a bit fancy, do the stiles along the back (above,,the vertical pieces) otherwise, just do it like pictured below. see how nice and clean looking it is? More ideas, search "trimming out kitchen island". you could try doing it in this color or if you feel like you want to have a painting party, do all of the cabinets in one, two or all four as they've outlined. This combo would look great w/your flooring. you kitchen ceiling needs to be skim coated and smooth out. or, have it retextured, primed and painted in a flat bright white. if you will be getting some retro fit recessed lights (Costco LED's,,,great price) then wait until the holes are done for those. Minimum of six 6" cans (8 would be better) , and two spots for pendants over the island. BTW, replacing the top on the island is a piece of cake. either check a granite fabricator yard for a remnant piece (you have a slender top so it should be easy to find) or look on craigslist for a remnant or even an entire island, or get an inexpensive butcher block and cut it yourself to fit. Whatever you get, leave an extra couple inches off the back end for an overhang. you could do a few more inches. The brick around your oven? paint it. white, black, gray, pick one. use a satin paint for that. clean and scrub that brick very well before you PRIME it (if using a dark paint, prime it with a gray primer. white for white,,,but don't skip the priming part) as for baseboards, if they're all small and short, pull them and replace w/these. Any questions? and yes, if you have the budget, call in a designer to help you out with what needs to be done, what should be done, etc.

So many things wrong with all that oak. It's much more than just the color of it. The window configuration around the fireplace is totally unconventional and looks odd, which makes the oak trim stand out as being more wrong. The oak cabinetry is not high end. The cathedral arches are out dated. The plywood oak ends look like low end oak with crazy wide tiger grain. The doors are full overlay with visible unattractive hinges. These are the most unattractive and cheapest options. The stairs are closed stringers with turned balusters. Closed stringers look better with square balusters. Open stringers look more traditional with turned balusters. The newel posts should be boxed and square, not turned. Craftsman stairs, using closed stringers, typically used boxed, large newels, and square balusters. Here you have a mix that doesn't work well. The floors are OK from what I can tell. Definitely paint the window oak....to minimize the weird lines of the windows. Get rid of the early American chairs. The main door is white with oak trim....The contrast is not good. Either paint the doors a darker, complimentary color...or paint the trim off white and then some tasteful accent color on the doors. It looks OK to have a stained door with painted trim....more so than the other way around. Never paint stair treads or handrails. Varnish/poly them always and always. Balusters and stringers and newel posts...are more optional.

Whatever happened to people putting gel stain on oak they don’t like? When I did my kitchen in 2003, everybody in the Kitchens forum was doing gel stain. It seems to me that those honey oak trim pieces are going to continue to scream their age out at you with every glance in their direction and it will look like you were too lazy or cheap to fix them (no insult intended, just trying to explain the effect they will have.). If you want to keep that honey oak look, fine. But you can’t fudge on it. You have to commit. Celebrate it. Or paint it or stain it. Don’t half re-decorate and think it will look good. Honey oak was just too....honey oak!

Regarding painting the wood trim. I agree, where do you stop is a big question. And it seems that your husband and perhaps even yourself are used to and attached to the look. So a 100% paint would not be an option. I would paint the baseboard though. It will instantly refresh the look. Having the baseboard same color as the floor creates some challenges, as it visually extends the floor upwards and connects it to the window trim. If you paint the baseboards you will have a much better definition of the floors and the window trim will be its own element. I would also add that its also ok to paint the window trim in some rooms only:)