Update...... A few weeks ago this got into my head again so I took both guns to work with me and took a caliper to both the Kimber, and Taurus. It turns out that the Taurus if a few thousandths smaller in all of the measurements that were keeping it from sliding into my holsters. This had me baffled because I know it litterally would not fit no matter what I tried. I went home that night and grabbed the leather holster off the dresser and tried again. Same results. The Kimber would slide right in with no effort, and the Taurus would not fit at all. Now I am going crazy by this point because I personally measured both of these guns and the Kimber should be the one with the problems. I put the guns in the safe and tossed the holster on my dresser and walked away.
Jump forward to yesterday. I wanted to do a little shooting and decided the Kimber got the position of my side arm for the day so I holstered it up and grabbed a few others and tossed them in my case and went out to the range. I finished my shooting and was packing up and decided I was going to give another go at the Taurus in the holster. I pulled the Kimber out and sat it in the case, and grabbed the Taurus. That fucker dropped right in the holster like someone custom made it just for that exact gun. It locked in like it was supposed to and drew out with the greatest of ease once retention broke. I tried it a few more times and it fit perfectly every time. When I got home I was putting everything away. I took the holster off and tried the gun in it again in my hands and it still fit perfectly.
Right about now I am feeling like a complete idiot, and I am not sure if it is because I couldnt get it to fit before or if it is because I have no explanation as to why I couldnt force it in before and now it just drops right in, but anyway, long story short, it works now and I am mostly happy. Its just going to be one of those unexplained mysteries that will haunt my dreams.