I suspect that in the case of my Bayfeilds that the toe box could have been reinforced better at the cap where it is sewn together. The cordovan is very stiff on these boots as was the sole (I also think this can cause creasing to happen in the wrong place) and the toe box seems weaker on the right toe, causing it to be the first breaking point of the leather.
Below is a pic from the original owner on what I think is the maiden voyage of the boot. When they boots arrived to me they still looked like this with no creases on the vamp, only the one on the right toe. The very stiff vamp leather seemed to cause a buckling of the leather at the toe making it crease. That part is weak compared to the left shoe and I have since formed creases in a more natural position to take pressure off the toe crease, this has helped already. As the natural vamp creases break in more, the toe crease should continue to take less stress.
I think it may be of some help, as someone mentioned, to maybe establish a breaking point on the vamp when new with a pencil in a more desirable position as to take stress off a possible weak point around or past the toe cap. I think I will try that on any new cordovan shoes I pick up, just in case.