You hit the nail right on its head! It's pretty bad that there is no skip all option, and for some of them you have to manually uncheck before continuing.
I'm in the same situation as you where I often work on fresh virtual machines, and so I see this a lot too.
The Pixel experience being stock Android without any bloatware appeals to me.
I've also always rooted all of my Android devices, and the Pixel has been one of the easiest to do so, though this advantage would only be relevant to a small minority of users.
I came across a similar pricing model for Prodigy, and it does seem like a sensible option. You pay for updates, but will always be able to use the versions you already have in perpetuity.
Mathematicians can have a lil doubt, as a treat