I have often worried about installing the T molding after paint etc, and presume its gonna be a "Do it right the first time" situation because any removal will pull something with it. It's just the nature of barbed stuff. I don't know if much of anything would help reduce it on older cabs because of the material used and how it has likely swelled a bit over time, making the mold tighter. I have noticed some T mold has thicker barbs than others, and have to take this into consideration moving forward.
Perhaps heating the T mold would make things more pliable, dry out the wood, and maybe help open things up some before removal? I have never tried or even considered it until now, but maybe it could be a way to make it easier to remove, and less damaging to the wood.