I've never been logged out, even on my headset with two accounts. I don't disagree that there's too much friction to just starting the thing up and playing tho

I've never been logged out, even on my headset with two accounts. I don't disagree that there's too much friction to just starting the thing up and playing though, and casting what you're doing - something I've only ever done once - doesn't work well. You can also use a tablet/phone with the Oculus app, for what it's worth. But still, you might want to try my suggestion. The strap is much quicker to adjust, the battery on the back balances out the weight, and if you had the dock with two batteries you wouldn't ever need to worry about charging the actual headset itself. Keep in mind that if you're only using it as your own personal device a lot of those steps/gripes go away completely. You'd only have the clear area steps and possibly resetting the play area, though mine usually finds it. My biggest personal gripe is how sometimes it just randomly decides to take an extra minute starting up, where you're in the passthrough type mode but it hasn't found the play area. I don't know if it's looking for it and can't find it, doing an update in the background, etc.