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.

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.

Thanks for the replies! My wife suggested we talk to a local real estate agent, so i think that is a good idea... just that Im not sure how helpful they are likely to be if we arent selling yet :) As for saving for our dream house, I dont disagree, however if doing this up nicely over the next ~5 years or so while we live here nets us some extra in the eventual sale, then that of course will help us as well. Interesting thing happened today actually. I got a knock on the door and one of the older neighbours asked if he could take some lemons from the tree. I of course said yes. Anyway he was telling me he had lived in the street for 40 years. I asked him if the house had always looked like this, and he said no that ~30 years ago the old old owner did a massive renovation and pulled off the timber and put up the bricks and gutted the inside of the house. Interesting stuff!

Thank you. My husband and I chose the tile (per recommendation at the tile store) and used a professional tiler (per recommendation at the tile store) for the install. It isn't a flip. This is a family home that we purchased and spent a year renovating—not DIY but with all professional hired help and a contractor to oversee the job. This tile person wasn't hired by him, though, as he was happy to use the person that we were told was very good by the tile store…. My heart is sinking. I absolutely hate the idea of retiling the shower as there is matching tile on all walls, including shower. I'm hoping there is some other idea out there that will help. I do personally think the tiler should have informed us if the tiles we supplied to him weren't suited to be mitered…we discussed it even before tiles were purchased and he didn't mention any specifications. I'm just worried now that if we put it on him to fix it, we'll end up with a bigger mess...