First be okay with the fact the bathroom tiles might need to be replaced. All of them. Replacing them in the bathroom will have the least impact on the rest of the house and whatever comes out in one piece, can be stored for future cracks. Maybe you can find a similar color but a different size, so it won't look too awkward, just an idea. Taking out a cracked tile is quite easy. Put on some gloves and safety glasses and (carefully) smash the broken tile with a hammer. An old screwdriver or chisel will help you tilt the pieces out. Work from the hole outwards to remove the other tiles. Removing a good tile is nearly impossible. Assuming it is still glued firmly, I'd say impossible. But, if you want to try anyway, you'll need to mill out the grout and then figure out a way to lift the tile..

If you are looking to keep the "period" look, then I say no. My place is from 1916 & had a gross 1980's reno. I ripped out all the ugly vinyl floor & cheap Sears sink & went with a black hex floor, white subway, dark grey grout on both. Toilet & tub were original, but I got an old "Standard" wall mount sink with chrome legs & towel bars & an antique medicine chest, light fixtures & glass shelving & towel bar off Ebay. My total job...about $5k. Help my tile guy is my neighbor, but those 10, 15, 20k bathrooms were out of the question.

Paint your house and ceiling first. You are probably asking for trouble if you put the floors down only to paint over the top of them. If you can, remove the tiles in the kitchen and paint just behind the line of the splashback too. Once painting is done replace kitchen benchtop then splashback. I would call the bathroom its own job and do it individually, unless you only need to paint the ceiling and if a tiler doesn't need to be brought in for anything else in the house? A lot of bathrooms now are getting tiled from floor to the ceiling if this is the case, paint the ceiling first, then tile. If walls need to be painted, it wouldn't really matter if you did them first or last, though if you did it first expect to do some touch-ups. I guess if you really wanted, you could do the first coat before tiles then second after... I don't exactly like stopping and starting painting, so I would do the walls (if they needed to be done) in one hit, after its been tiled. Well that's the order in which I would do everything... Really, for what you're asking, the painting could be done at anytime, but to make life easy on yourself, I would definitely recommend doing it before the floor.

I'm finding it a little hard to see the detail. Can you enlarge the top 2 plans?