I agree with you the pillars are unfortunate. The replacement tiles will stand out no matter how close they come to matching so you're better off making sure they are clearly different so the gray one is better. Putting busy mosaic tiles could look nice but will interrupt the flow between rooms which I'm guessing is your problem with the columns in the first place. You will need to create a dextrous solution to tying into the 2x4 wall on the left side but I think it can be done tastefully- maybe beveling it back once you get past he end of that wall.

As chookchook said in her recommendation about painting, put a drop cloth on the floor. Get a very safe ladder. remove the lightbulbs, and cover the outlets. Turn off the electricity to the chandelier. Then spray it with a mild cleaner (I use one I found at Target that's basically water with vinegar, until it's dripping wet. Start at the bottom and work your way up, so you don't have dirty spray dripping on the bottom of the chandelier.Work your way up and down until the dripping spray is clean. The chandelier may be gorgeous and expensive, but it seems totally out of place in the architecture of the room--more at home in a chalet than a sunny room with a window wall. I would probably try to find a way to get it removed, and sell it to someone who appreciated it better than I.

Love blue tiles. Depending on how much sun and how hot your pool gets in the summer should dictate what color it is. We live in Arizona, so cool blues work best. Our neighbor has brown tile and a dark pebble tech pool. Looks like a swimming hole and gets really hot - 94% water in the summer. They obviously didn't think it through.

Excuse my duh-ness but i'm having difficulty trying to follow whats going on here. Are these two photos an exact replica of your house and pool ? If not a hasty sketch with dimensions could help a lot. By kitchen wall do you mean the wall behind the bar ? And where is the pool wall ? Are you considering the covered area as being "inside" ? Sorry for all those questions lol Sometimes when you have a design problem you need to turn it inside out or on it's head. If you can't beat it maybe embrace it by making a feature of it : i.e. contrast by having the lightest colored pool surround and a great blue or tile inside and under the overhang, something that will echo the water color ? If you have a great covered area as in photo you'll most likely be spending a lot of time there and it could be soothing to be able to sometimes retire into a darker inside. In my book, 10M isn't small and also contrasting two floor colors doesn't necessarily make a space seem smaller and confined and may in fact even open it up. Could it be that you've thought yourself into a box here ? Sometimes one needs to give it all a good shake up and see how it resettles.