I think your experience depends a lot on the shape of your head which you can't try out before buying. I also have a Rift S and going to Quest 2 I was pleasantly surprised. It kinda sits on my forehead not touching my small cheeks at all. And since most of the weight is on my forehead, it's comfortable enough that I don't really notice the headset while using.
I pretty much put it on and I'm good to go. Everything's clear, much more so than with Rift S and the strap is good enough for my short hair. I've noticed it tends to slip up and come off of your head when I've put it on people with long hair. One tip I could give you is to adjust the angle of the headset for better clarity if you need to. Just kinda rotate it so the screen isn't aligned 90 degrees or smth relative to your face.
Oh, and you should measure your IPD to get a definitive answer on what would be the best setting for you of the three. Mine's 68.9, so the third one is pretty much perfect for me. Here's a nice tutorial how to do it yourself: https://www.wikihow.com/Measure-Your-Interpupillary-Distance