I recall seeing some (non-Apple) hardware with case-to-cable transition designed as an inverted strain relief. Instead of a semi-rigid tube extending from device, the function was performed by proper curvature of the hole itself; nothing extended beyond the profile except the cable.
I'm having hard time describing it properly, but the hole walls had specific profile, elliptical extending outward. Pretty much like the big end of a trumpet. The most you could bend the cable was to make it touch the hole wall, and that profile of the wall was good enough to prevent cable cracking.
One disadvantage is that this kind of solution takes up some space insede of the case...
I'm having hard time describing it properly, but the hole walls had specific profile, elliptical extending outward. Pretty much like the big end of a trumpet. The most you could bend the cable was to make it touch the hole wall, and that profile of the wall was good enough to prevent cable cracking.
One disadvantage is that this kind of solution takes up some space insede of the case...