scenery matters
I've had luck with both, though I agree it's useful to have the sun behind the camera and that's my default.
I don't know the ground track for this route (any pointer welcome, I don't know how variable flight tracks are, I don't fly often enough).
For Oakland to Denver and back, I think Mono Lake and Yosemite are likely visible, but don't know which side to try for, in either direction.
Other reasons to take one side or the other depend on particular interest during takeoff and landing -- city views. Of course flight track depends somewhat on the weather at the time. But I've gotten some nice backlit thunderheads, for example, from the sunny side, and climbing through clouds backlit by sun is dramatic.
Of course the odds are best on the shady side -- no chance of a glory without seeing your own shadow.
My favorite didn't-have-a-camera image:
Atlanta, takeoff a bit before dawn in fog, and we turned over the city and it was a smooth, flat, pearly gray sheet without a visible ripple, the fog just flowing like a sheet very slowly -- except for a couple of places where the city skyscrapers were just barely poking up through the cloud, the antenna masts visible, and downwind from each was a beautiful long alternating ripple, the vortex, lit by the sunrise coming flat across the fog.
Sometimes photography doesn't need a camera. Still I wish I could share that image better. Wonder who else has seen it and how common it is.