I don't wear glasses so I can't comment on that, but I did upgrade from the stock strap to what's known as a "frankenquest" setup, where a Vive Deluxe Audio str

I don't wear glasses so I can't comment on that, but I did upgrade from the stock strap to what's known as a "frankenquest" setup, where a Vive Deluxe Audio strap is connected to the quest via 3D printed adapters, with the counterweight velcro'd onto the back strap. As far as comfort goes it's not bad and the headphones on the Vive's strap are a solid upgrade from the Quest 2's directional speakers, but I'd still prefer for any headset I upgrade to in the future to be more lightweight.