OWB is the most comfortable without a doubt however for me IWB has always been a compromise between concealment and comfort. The most discomfort is when driving and so I shift the entire rig more to the 3 O-Clock position from my 3:30 normal carry. The best you might get is with the Crossbreed because of the large leather backing. The position of the rig in the pics looks good. Try moving it more to 3:30 and see if it feels any better.