Also, in your second to last picture, it's back too far. See how your girth is slanted? It should run almost straight up and down, right behind the shoulder, the girth should fall right behind the armpit area (if a horse has armpits) but still leave room for shoulder action. The skirt is right up on his flank and it shouldn't be. That's a no fly zone - you don't want anything rubbing or irritating a horse at their flanks or you might get to experience a rodeo bucking bronc event.
Don't let sweat patterns fool you. Just because a horse sweats a clean pattern under a saddle, doesn't mean it fits.
Have you noticed any really smooshed looking spots when you pull it off? I know if we ride this one Billy Cook ranch saddle we have on Sarge, when I pull it off, he has a spot on each shoulder where the hair is pressed down hard and he'll be tender there the next day (So we never, ever ride him in that particular saddle - he's just too big).
"We are here to laugh at the odds and live our lives so well that death will tremble to take us."