I've had an Oculus Rift for several months now. So far, most of the games I've played on it are ones that I'd play for 30 minutes and take a break. Recently, however, No Man's Sky released an update that supported VR. This is something that I find myself playing for well over an hour at times. Because of this, I've been noticing pressure building up on my face that keeps me from enjoying the game. I've tilted the visor to distribute pressure on my forehead and cheekbones as evenly as possible. The velcro straps on either side are giving as much slack as possible. The strap on the back of my head is positioned low on my head as others have recommended to me before. I lowered it so low before that the straps pressed down on top of my hears to little effect.
I can gently grab either side of the VR visor and pull it forward and hold it in place with my fingers and get perfect comfort. Little to no squeeze at all on my head. But the second I let go, the squeeze returns and I dread playing with it on as I know I'll get a headache. I'm guessing there are springs inside the headband behind the visor to ensure there is a snug fit (to ensure the headset doesn't fall off if I look down quickly). I've even though of wrapping duct tape around the headband to hopefully prevent the spring mechanism from pulling the visor down on my face.
Also, no, I'm not very enthusiastic about getting a Rift S. I've heard it's more comfortable, but I'm skeptical about having sensors only working in front of me. I already have 3 sensors set up in my room that have excellent tracking.
I have a Quest, with a similar head strap, and I can relate. After prolonged use I have marks on my face. I don't think there's a simple solution.
But I have used headsets with the "halo" strap, and there is no pressure on your face whatsoever.
If tracking quality is stopping you from buying a Rift S, it shouldn't. I can say from personal experience that the Oculus Insight tracking is fantastic. It is superior to other inside out tracking, like on the WMR headsets. My Quests tracking works flawlessly and the Rift S would be even better with it's extra camera.
If you haven't tried a Rift S yet, I would highly recommend it before you discount inside out tracking.