I went through the entire process multiple times to make sure it wasn't me:
Set t19 length using my dial indicator tool setter
Set t23 length
Use t23 to set Z zero on my part
Switch to t19, Z zero is now off significantly
Switch back and check with t23, Z zero is off the same amount.
verified without physically changing the tool out or moving the Z axis at all that the same thing happened. (set t19 length, set Z zero using t19, switch to another tool via the menu while leaving t19 in the spindle and the Z axis in the same spot, switch back to t19 via the menu, Z zero is now off)
The tool lengths were correct after re-measuring them.
Eventually I rebooted the PC and cycled power to kflop/kanalog. The problem vanished.
Any idea where to look for potential issues? This kind of a scary one to have randomly pop up; I am running the program now and verifying zero is still correct after every tool change.

I'll respond when it is finished and attach my toolchange program and tool height set program