I'm running Tubeless on my Aeolus 5's. I really like it but when I got a flat, I just had someone pick me up. Once i'm out of tubeless juice, i think i'll go back to tubes. Take some pictures on your ride and show us what you saw!
I'd ride the new wheels, heck, what better way to enjoy new gear than all day on the 'big ride'. But I'd set them up however you normally run your current wheels. As noted above, nothing ruins rides like sitting on the side of the road googling instructions.