#1 is really nice. Lady seems really part of her work, and you've caught this well. Must have been in at least partial shade. As for the little Catholic schoolgirl skirt... no wait, that is another thread. I suspect the polarizer will not be much help with this kind of high contrast situation. Miserable light for shooting people, and I don't do it enough myself to have real good answers. Cloudy days are best. Some shade, or even backlight (sort of like #3), will get rid of the harsh shadows. When the subject is then lit by a broad expanse of blue sky, sometimes need a "skylight" warming filter helps. In theory, this is what flash on camera should be good for. I've not had much experience using it.