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.

I do not have any tiles in my current house but if you think about grout discolouring and looking bad.... then I think that might answer your question. My thought - the less grout the better.

I wouldn't do skirtings . I'd do the floor tile for '1 tile' up the wall ( assume they are 200 x 200 or 300 x 300 -- cut them if 400 or 600 ) . Personally , I'd probably even do the 'silver' tiled areas in that 1 height darker tile too , as it would make the whole room look more 'level' , but thats up to you and your tiler .

Used beveled subway tiles for whole bathroom without thinking about internal corners so the corner looked terrible then the silicon went on and it still looks terrible I guess apart from an aluminium strip or a marker to go across the silicon there aren’t many options