My first Rift did not sustain damage from strain while wearing it, but rather when it was store in the case. Be sure to put the Rift in first so its cable can bend gradually and can sit in the bottom of the cutout UNDER the other cables. Putting the Rift in the case last causes the Rift cable to go on top of the stack of other cables, forcing it to bend sharply at the Rift strain relief.
Also, the Strain relief is a poor design in that it would be more flexible if it were shaped a bit differently, allowing more flex. The existing strain relief could be modified by clipping out some of the plastic between every other disc in an alternating fashion, so that a pair of discs is supported only on opposite circumferential borders allowing tangential flexing at that joint, with an adjacent pair of discs having the other pair of separators removed to allow flexing at a 90-degree offset. Difficult to describe but a picture would be much better. Google to the rescue... here is what I was picturing in my mind's eye:
Another method is to use a strain relief with spiral cutouts also allowing controlled axial flexure, such as this one:
Notice how the Rift strain relief is designed with supports on all axes to PREVENT flexure, thereby increasing strain where the cable exits the so-called strain "relief" (really a "strain concentrator" in this case).
I reported this issue long ago to Oculus and I was told that it was redesigned, but my replacement Rift suffers from a similar (or identical) strain NON-relief device...
Just study the ridges in the existing Rift strain relief and see for yourself how it was mis-designed. Image how it concentrates force on the cable.
So, either cut out some excess plastic to allow the strain relief to flex, or add some extra (flexible) support to it. But whatever, be careful packing it into the case to prevent excess cable strain.