Ok, so I got some photos today- let me know what you think. I also tried a thicker pad, and that seemed to help a lot.
This one is when he's tightly cinched.
This one is with the thicker pad
And these ones are in the saddle
I couldn't get any without a saddle pad, as if the saddle gets dirty, I cannot return it.
It seems like if the cinch was back a bit more, it would fit much better.